looking for similar guidance, i found a 70k to 90k value estimated home, listed for 55k only work that i can tell from the pictures is updating the wallpaper to a basic egg white paint and i can do that myself in a 2 weeks or so.

My guess is you have a car payment and eat out a lot? 

First few years, depreciation will eat most of your income so you might have very little to actual tax savings from the rentals.If you dont have a w-2 job, your rental income determines your income tax bracket.

I can eat a $10k-$20k unforeseen expense (Contamination, burst pipes; etc etc) when my profit is $100k+.

Because of this, I'm missing out on good opportunities because somebody else is eating me to the punch.

I would love for him to not have to worry about a college education and student debt and I would love to be able to leave him a small nest egg when I'm gone.

I guess I'm curious what your own threshold is before you say as the property owner "just replace the damn thing, eat the upfront cost, and stop sending someone out there to unclog the sink."

The fines will eat up at their profits.

On a few numbers I have looked at they seem to lack closing costs, which will significantly eat into the numbers, so make sure you take that into consideration.

This why vetting upfront is so important.On the other hand, a larger contractor may have real assets in the company or even a reputation that they want to protect so they want to find away to avoid getting into legals which waste time and money for them.With respect to contract size, in reality anything under 100K is not worth a full blown lawsuit as the legals will eat you alive even if you win; small claims court may be your best bet if you are OK managing the process or maybe using a paralegal.On the emotional side, I strongly urge you to put that aside.