Really, I only have 4 tips for you.

1. Contract Overview: pressing TAB will bring up the contract details for you during a contract. This is useful for obvious reasons, and I didn't figure this out until I had all but 1 of my perks purchased already.
   
2. Satisfaction rating details: I have found that having <40% satisfaction rating leads to having only 1-2 contracts available (usually only 1). At 40%, you'll see a jump to 4, and at 50% a jump to 6. While working for the Solid Work Force achievement, you'll want to be working as well to keep up the rating - I recommend shooting for 50%, so it remains AT LEAST above 40%. This will ensure that you can keep sending out (un)handymen on contracts, angering other customers, at a constant pace.
   
3. Save often: The game bugs out, and in the case of the freezing while providing your handymen with gear, that means restarting the game. I recommend saving after at most 2 re-gearing in a row.
   
4. Tool Assignment (for contractors): Contractors fail when they don't have tools, which makes sense. However, there is no way to have them resupply automatically, or even tell you when they've exhausted their supplies. As such, I recommend assigning the necessary supplies/tools while assigning the contract. This helps eliminate the "misses tools" failure message, and is overall a huge time saver.
   
5. MONEY: you can multiply your money by using your contractor's discount/s and reselling what you purchased - namely, those from the brand IKA. I found this information first on TheBeowolf»EC«'s guide "Infinite Money", which (though bare-boned) you can find here. I'll provide some more information here, however:

I'll lead with the pertinent achievement:
This one will come very easily and quickly using this method of making money.

In order to maximize your savings, and therefore make a better profit, the following skills are necessary (and I would recommend that you focus on these first, as quickly as possible).

1. Hard Discounter 1/2 (no prerequisites needed) x0.9 buying price.
   
2. IKA's gourou (some prerequisites needed) x0.6 buying price for IKA ONLY.
   
3. Hard Discounter 2/2 (MANY prerequisites needed) x0.8 buying price.
   
4. MagicalWoodWorker 2/2 (some prerequisites needed) 10% buying discount for wood furniture ONLY.

The way they stack is like this: the highest Hard Discounter * IKA's gourou. So if you have HD 1/2, then you'll be paying 0.90*0.60 = 0.54 of the stock price. If you have HD 2/2, then you'll pay 0.80*0.60 = 0.48 of the stock price. (If this is confusing, just check out the table below).

Here is a table showing the IKA products at prices as you gain the skills in the above order, showing profits in brackets. Sell prices don't change, so they are listed first. Since it seems you cannot get the IKA's gourou skill without Hard Discounter 1/2, I don't include it separate. I just stuck with the Bathroom Sink.

(The letter before the item name indicates where it is found: K=Kitchen, L=Living Room, B=Bathroom)

- MagicalWoodWorker 2/2: This adds another multiplier of .9 for wooden furniture products. With all of those skills, you have the no-brainer Bathroom Sink, as it benefits from all of these bonuses.

*** Yes, I know, this is weird. But I don't know why it does this. I verified this in game.

There are 2 missable achievements. If you want to play it all in 1 playthrough, make sure to pay attention to these. I've ordered them by level of inconvenience.

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There is only 1 achievement that is missable and also a big PITA, since it's endgame related. I'll keep most of the info on it in the PITA Achievements section, but be forewarned: do not run out of money before you're ready to complete this one. If you do, and elect to stay in game (the game calls you a cheater), then you won't pop this even later.

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The other one isn't a big deal to start a new game to play the tutorial again. In fact, if you missed it already (like I had), just wait until you have only this one and Money Doesn't Grow On Trees left - the latter will erase your game as it pops, and you can go back to this one smoothly:

Just make sure to 100% the tutorial job and you'll be fine. FYI: this will require you to purchase an item that is reparable to replace it instead, and also remove another item.

If you are having trouble getting this one (for those who are not familiar with the game yet, and trying to get this 100% in 1 playthrough, etc.), the deviations can be found below:

1. Perform all repairs
   
2. Be sure to use the preferred color for painting the kitchen (pink, in my case)
   
3. After repairing the fridge (which is forced on you), remove it. I believe you can sell it, but I simply put it into my inventory.
   
4. Remove the kitchen top (which was above the fridge) to make space for the bigger fridge.
   
5. Purchase the preferred fridge (Bios brand), and place in fridge spot.
   
6. Double check everything checks out (see my screenshot for a hand-holding).
   
7. Ding!

Also note that you will net a MUCH more meager profit due to the increased cost of the preferred fridge, so if you have to restart the game (say, due to Money Doesn't Grow On Trees not popping) but already have this one, don't bother with it. Of course, the tutorial is also skipable (see menu), but I don't know if you get any starting funds this way.

No, there is no story here, but you will inevitably get these achievements as you're going through the game. These first two cannot be missed even if you try, if you are going to use every feature of the game (namely the end game, handymen).

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There's a reason why this is the most achieved achievement: finish the tutorial job. Keep in mind that while in the tutorial, you should also shoot for Apprentice Handyman.

You literally cannot proceed to the "endgame" of hiring other managers without this. Select and purchase any perk.

Also literally impossible to skip on the way to the "endgame".

It is rather difficult to miss this on most contracts, as long as you are working on the tasks. If you miss this the first few contracts, just wait until you get more acclimated to the work and have all your tools - it'll come easily.

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You don't really need any help here. Heck, this is probably text that will never be read.... "Finish a Contract By..." are both easy achievements that are mutually exclusive per contract - you need at least 2 contracts to get them both. Naturally, you'll be doing a LOT more than 2 contracts...

Throw money at the problem. No problem.

If it ain't broke, don't fix it. But if it is - well, fix it.

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I don't know how people get People Pleaser without getting Certified Handyman at the same time... Just complete the contract with preferences, and quickly, I guess... On the other hand, shoot for all of the following in quick succession.

If you're here on this guide, you like to complete things. Complete 5 contracts with preferences also completed. Easy enough, and you'll get this before you're watching for it.

Again, you'll get this before you can even realize it. While you're at it, make sure to go all the way and get the following 2 achievements with perfect satisfaction:

100% satisfaction rate total. This is useful to start with when you start spamming handymen because... well, they FAIL to satisfy.

HOWEVER, make sure you get this PRIOR to hiring any handymen, as the grind will have you forget about customer satisfaction. Terrible, isn't it? (On the other hand, how many contracts you have available to you seems directly related to satisfaction level, so be careful....)

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This one is ridiculous: there is hardly anything available to customize with. Dream house? Please...

I believe you just need to put something down, but I got this before I noticed. I did the following:

• Got rid of 2 pieces of furniture
  
• Placed 4 pieces of customized furniture (colors, etc. on kitchen cabinets)
  
• Moved 1 piece of furniture) trash can
  
• Painted walls around TV room.

If you test out what is required, comment and I'll add it in.

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Here comes the manager section (mind you, the easy, non-PITA part)... Your handymen need to be geared up to avoid the whole "So-And-So failed to work on his contract. He misses some tools." (I still get these problems, so I don't know if this actually helps, tbh...), which is why we begin with:

You probably have already done this for yourself, but even if you hadn't, you'll be doing this for all of your handymen. You'll need money to do this, though not as much as you might expect. In any case, follow the IKA reselling (exploit?) to rack up the cash.

The first of the horrible, useless, pathetic handymen. And no, I have not noticed any productivity increases for getting the higher rated (more expensive) hires.

The second of the horrible, useless, pathetic handymen. I'm sure you understand by now.

The last of the horrible, useless, pathetic handymen. But the horrors are not yet over... Make your way over to the PITA section next.

Here they are: the achievements that are elusive or otherwise a big PITA.

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These first two are annoying because of how terrible the UI is, as well as how long you actually have for contracts. Before you get started, know that the contract timer is in the upper right of the screen (while on a job), right beside the contract icon, and also that you can see what the time limit is for the contract by going to the contract list (using the phone) and clicking on the additional details for the contract (the three horizontal dots). Now that you know where to get the info...

This is how I got it - in as hands off a way as possible:

1. DO NOT perform any of the contract.
   
2. Wait in game, in contract, until the contract timer and icon turn red.* This is just past x2 contract duration. Go make yourself breakfast with bacon and cheese - spoil yourself, doesn't matter if it's dinnertime. Everyone loves breakfast...
   
3. End job - WITHOUT performing any of the contract. (I'm not sure if you get it if you do the job.)
   
4. Ding!

* Thanks to Jerry_BCN and the hint he offered in his discussion post to finding this out.

The contract time is much more important here. End it on exactly the minute it hits. REMEMBER that it takes another click to confirm the ending of a job. So step-by-step:

1. Perform ALL of the contract.
   
2. Wait in game, in contract, until you are a few seconds (IRL) away from the contract duration. This will give you enough time to...
   
3. Open phone and End Job.
   
4. Confirm the ending of the job AS YOU COUNT DOWN TO 0 (in your head, phone timer, etc.)
   
5. Ding!

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!!! NOTE: Check at the bottom to see possible (easier) options by other players.

This one is not very clear on when it is available to pop: I tried it 5 times. Here is what I was able to learn:

• You must already have contractors available. (Every time I tried prior to unlocking contractors, nothing happened.)
  
• You must bring your money down as much as possible. (I got it to $0, by buying bathroom sinks, and then tools that eliminated all funds.)
  
• The alert for the achievement pops up at midnight (that's 00:00).
  
• When you see this alert regarding a pending bankruptcy, click YES. DING!
  
• When you see the following alert, the achievement likely won't ding: (When I got this one, I hadn't gotten the Solid Work Force achievement yet, so I elected labeling myself a "cheater" by the game in order to continue. The achievement doesn't pop this way - but be warned, selecting the other option erases your game. To get it though, I got this again and elected to erase the current game so I can start all over. Doing this does not directly pop the achievement; it's a different alert.)
• If you get any more information on this, let me know and I'll edit this.

Player lostnight has reported that you can get this one more easily - I'm not sure why my playthrough didn't function this way, but this would effectively make this NOT a PITA achievement:

1. (No need to wait for contractors!!!)
   
2. Spend all your money
   
3. Wait for your rent bill to hit, while failing 1-2 contracts
   
4. Same alert as above, regarding a pending bankruptcy, and click YES.

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This is the biggest PITA achievement of the game (assuming you don't mess up on Money Doesn't Grow On Trees like I did...). There is no way to track your progress. There is only one way to (noticeably) make your (un)handymen more effective or efficient, which is also a pain to manage. And every time your contractors screw up, you have to work on getting your satisfaction rating repaired, just so you can send more of them back to customers to screw it up again. It's okay to be pissed at this achievement, and at the developers for bringing this stupidity upon you. I wish you luck.

1. Get your rating as high as possible while still within the bounds of your patience.
   
2. Hire a bunch of these worthless, unskilled bums.
   
3. Give them one of all the tools that you work wonders with.
   
4. Send them out on jobs (and wherever you can, might as well pair up jobs to specializations. Not that it's clear AT ALL.).
   
5. Repair your satisfaction rating as it diminishes.
   
6. Send them out as they return, but be sure to "assign" them tools they need for the job.
   
7. Repeat....repeat....repeat....
   
8. Ding. Finally.

Keeping your contractors supplied properly will result in higher success rates and thereby steady your satisfaction rating, so definitely don't ignore it. There is nothing you can do to automate this, nor is there anything you can do about them pretty much always being late. Slackers...

The following are credits to information this guide has benefited from.

• TheBeowolf»EC« and his guide "Infinite Money".
  
• Nikissus, who pointed out the most lucrative item to sell in TheBeowolf»EC«'s guide.
  
• Jerry_BCN, who asked and then later answered a discussion post for the Somebody Got Mad achievement, titled "how to make a customer become mad??".
  
• lostnight and his tip on the Money Doesn't Grow on Trees achievement, which is much easier given that you don't have to wait for contractors.