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A Personal Rant: I Can’t Stand Working with Contractors!

A Personal Rant: I Can’t Stand Working with Contractors!

9 min read
Ali Boone

Ali Boone is a lifestyle entrepreneur, business consultant, and real estate investor, who has literally defined non-c...

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Yep, I said it.

I absolutely, in no way, enjoy working with contractors who do work on my house! I understand that a lot of you do, and that is totally fine. I can see the appeal and where it could be fun to rehab or fix up a property that you’ve bought, but personally, I can’t stand it.

A lot of real estate investing revolves around fixing up properties. One of the best things that fixing up a property can do is force appreciation. On a more minor scale, people fix up properties just because they need some work done on them due to normal wear and tear or whatever other reason.

Hear Me Out

When I talk about contractors in this article, I’m putting more emphasis on the former as I’m thinking more in terms of doing improvements to properties than I am repairs. Contractors doing repairs for me rarely bother me, because the item is either fixed or it’s not. If it’s not, I tell them to come back, no problem. But improvements, such as anything requiring specifications of any level, is where I have the problem.

It’s fixing up houses, i.e. doing these improvements, to either sell or rent the property out that plays such a big role in real estate investing. I get it, I get why people want to do that, and it makes total sense to me. Do I want any part of it? NO.

Don’t get me wrong, contractors are far from the only people in the industry that can be frustrating to work with.

For example, property managers especially have a bad rep and can be difficult to deal with. For me, though, property managers are easier to manage than contractors because it’s the management style or technique that has to be dealt with. It’s a slower-paced managing of those guys, whereas contractors are a fast-paced group because they are working project by project — and get paid per project rather than a slow and steady on-going pay structure.

Then, of course, the big one with contractors is that you can see the results, visually! If a contractor paints the side of your property, you can see if he did a good job. If he fixes a leak in your roof, you can see if it still leaks. The latter is more of an example of repairs, but you get the point. I guess if you want to get technical, you can “see” a property manager’s work too, but in this case I’m thinking more in terms of the complication of needing a contractor to redo something versus just telling a property manager to adjust something (which isn’t necessarily a redo, and especially not a redo that could potentially cost you more money, as could be the case with a contractor).

Related: My Plan to Optimize Contractors and Begin Taking More Control of Repairs

Whatever, you get the point. So where all this is coming from is that I just recently hired a contractor to do some work on the house that I currently live in and the whole thing has been nothing but expensive, unsuccessful (so far) and stressful. Most of my day(s) since the work started have been taken up by this situation.

Do you know how many other things I could have been accomplishing in that time had I not had to use all my brain power over this contractor situation?

I’m going to give you two quick examples of times, including this one, that working with contractors has stressed me (and my wallet) to no end and in the end never even gave me the product that I was hoping for.

Contractor Flop #1

When I bought my very first house (personal residence) in Atlanta, the first major improvement I wanted to do was a driveway addition that extended around the side of the house so that multiple cars could park in the driveway.

The addition would allow some cars to pull to the side of the house — still on the driveway — with enough room to be able to get out around the cars behind them if necessary. I went over all of this with the contractor, and he swore he understood exactly what I meant about needing the cars to be able to get out around each other (meaning, the extension needed to start out in front of the side of the house in order to give enough spacing).

Sure enough, some $5000-something later, I had the driveway extension around the side of the house, but it started too close to the house, which caused it to still only allow a single-file line of cars in, so no room for anyone to get out. I addressed this to him, very obvious in my concern about the major missing part to the driveway, and he said there’d be no way to add that part in now that the rest of the driveway was done. I would have to hire it as a whole new job, i.e. pay for the addition as an individual job and not part of the other extension (meaning, expensive) and other than that, “Oh well” — nothing he could do.

Are you kidding me?

I just spent $5,000-something dollars on a driveway extension that didn’t meet the biggest requirement I had for the whole project in the first place. Granted, what was done was nice, but even then there was a ridiculously sharp drop-off that he didn’t fill in that I wasn’t happy about. I had no options of anything that could fix it unless I wanted to shell out another few thousand. No thanks!

To this day, cars can’t get out around each other in that driveway.

Contractor Flop #2

This is the one from this week. It is only about a 10% of the cost of the driveway project, so not nearly as detrimental, but stressful nonetheless.

All I needed was bookshelves built into my wall to hold my books. I had the property carpenter, who was planning to do it, but he’s so busy he couldn’t get to it.

So I went contractor shopping.

Related: The 5 Most Common Items Found in Contractor Lingo

I mean, building bookshelves on a wall is far from a huge project, but due to the weight of the books, I knew I needed something very substantial and sturdy, which is why I decided to trust a professional rather than myself (I’m notorious for screwing up anchors in walls and making big holes, but I can usually get away with it. But I wasn’t going to risk that for books because they are so heavy).

Then I thought to myself, well if I get someone to do the shelves for me, while they are here anyway, I will go ahead and have them fix some other small things around the house — touch up paint on the walls, hang a more sturdy bike rack than what I have, hang a surfboard rack…everything that needed to be hung in studs.

I had all the parts and racks, I just figured, why not let the professional do the drilling for me? The surfboard hangs over my bed, and the last thing I need to happen is a surfboard landing on my face in the middle of the night because I suck at putting anchors in walls. So, very minor things in addition to the bookshelves.

I found a contractor I loved. She (yes, a she) seemed impressively knowledgeable, and I liked her vibe, so I hired her. Most definitely, she really is skilled. The bookshelves are so cute and amazing-looking; she made them custom out of wood, and they will have no problem holding up my books.


She went to Home Depot to get the wood and have it cut. Their wood-cutter wasn’t working. So they had her rent a table saw to cut the wood herself. Well, that’s great and all, and she cut the wood perfectly, but that forced me to compensate her for the saw, and it added multiple hours to the job, which essentially got held over my head for payment purposes.

We were also down one shelf because we had a miscommunication regarding how many shelves there were supposed to be, but the saw had already been returned (I’m still down the one shelf and have a huge piece of wood sitting in my living room needing to be cut for it), and everything just started getting frazzled.

On top of that, the paint I bought for the shelves ended up not matching the walls despite ordering the exact same color as is usually used, so now I have walls that are multi-colored around these shelves. The contractor also didn’t bring drop clothes, so I have paint speckles all over my desk that I can’t get out. Then, because the wood cutting took so much longer than planned — and then there was the discrepancy about the number of shelves and how to place them — everyone was exhausted by the time any of the other work could be done.

We got the bike racks up, but no surfboard, no repair of another shelf I needed done, nothing. So I’m still sitting in a complete mess of ugly shelves because of the paint, shelves I can’t use yet until we repaint, a surfboard on the floor, wood in my living room, paint all over my desk, and nothing else fixed that was supposed to get done.

Now, she says, I will need to pay her an extra $100 to do the extra shelf. No way around it, she says.

I even asked if I could have her just forego doing the extra work (surfboard rack, etc.) in place of just finishing the one shelf. I have to have that shelf because there is a space missing for it on the wall, plus she’s the only one who can build it because it’s custom work (I mean I can probably find someone else to mimic her other ones, but that’s a whole other stress). And it’s not that I don’t have $100, that’s not the problem at all. But she already charged me, in my opinion, way too much in labor for doing the shelves already, so the thought of paying her yet another $100 on top of that just makes me want to walk face-first into a wall (or a bookshelf).

Plus, while I had a part in the miscommunication about how many shelves we needed, I did not have a part in the decision to rent the table saw and have to do everything manually. I would have told her to go to the Home Depot five miles from the one she was at and have them do all the cutting. I didn’t choose to do everything the hard and ungraceful way, she did. So for me to have to put more money into all of this? You must be kidding me! I can’t do it. The irony too is that I was blatantly trying to go the more cost-effective route with this whole project since I don’t plan to live there for more than another year or too.

Oh, add to all of that, I’m the one now who has to get the wood cut because she didn’t have a truc,k and the remaining wood wouldn’t fit in her car. So if she comes back to do the extra shelf, all of the wood will be pre-cut for her (via me, the client!) so she just has to screw it all together.

Seriously! I’m getting fired up thinking about it.


Props to all of of you who enjoy rehabbing properties.

I am not one of them.

You are probably better than I am at dealing with contractors and communicating with them and getting the results you ask for, but I can’t seem to get it right. It’s bad enough I’m a perfectionist, so looking at the paint splats and multi-colored walls right next to me as I type this is just beyond what I can stomach, but even if I weren’t a perfectionist, the stress associated with having someone who does their own thing despite my requests and charges me an arm and a leg for it is too much for me.

People can argue all day long that if you aren’t fixing up an investment property to force appreciation that you are making a bad investment, but I don’t care. I will not buy properties that are fixer-uppers. Maybe someday in the future I will be sitting around bored and decide to take on that kind of project (there is some appeal in being able to fix up a property that could make putting up with contractors tolerable), but for right now, I’m way too busy. I have a business to run, I have a ton of activities I’m always doing, and I just have other things I’d rather think about and I don’t want added stress to my life.

The properties I buy, yes they may be slightly more expensive, but they still have positive cash flow on them and any repairs they need are very minor. Therefore, no stressing over contractors doing improvements on them or having to manage anything about them.

Rock on to all of you out there who do it that way, but I’m too busy for it, and if just having a contractor try to build book shelves in my house could be so stressful, rehabbing full properties is definitely not something I care to take on. To each their own, but I am quite content buying houses that don’t need rehabbing.

Phew! I feel better, thanks for letting me get that out of my system, BP.

If any contractors in LA are reading this and want to come fix my bookshelves, come on! (Okay, knowing I don’t want to pay $100 for it probably isn’t enticing, but it’s her I don’t want to pay $100 to, not you.)

What’s your experience with contractors? For those who love rehabbing fixer-uppers, we want to know — what do you love about it?

Let us know in the comments below!