That way there won’t be any discomfort to an extent!

Sounds like you should keep pressing forward and lean into your discomfort! 

This is where you would buy a property as primary residence for as little as 3.5-5% down and then implement the same strategy you are using in your current home by renting out the rooms, basement or ADU (the more creative you can be and more discomfort you can live with the more cashflow you can achieve).

The only issue is the discomfort that may occur should you bump your head on one while working underneath.  

Education is important, but it is essential to be comfortable with discomfort, and to be willing to learn as you go.  

I'm pretty sure that's where my nagging discomfort has been coming from when considering that method. 

Once you get their insurance companies involved it is a whole different level of discomfort for the contractors and they may be forced to respond.

List the past few items that have become a problem because he did not report them promptly, and how they ended up causing him discomfort, caused you stress and why this is just not the way to do things..

You should only really do it if you love it, or are willing to put up with a lot of discomfort for a good profit!

I know there will be moments of discomfort and things will pop up that we might not expect, but just as I said to Luke, you have to start somewhere!