This will be critical, because you don't want too complicated a process that the insurance companies overcharge you (not sure if this could be an issue but it strikes me as a possibility)- Lender. 

Many people: aren't mechanically inclined; are scared of heights; get sick from small stinky black mold stuff (plumbing); etc etc etc ...

As always, I'm open to any advice and constructive criticisms! 

The only reason I am responding back to you is to encourage you to think critically on every recommendation given to you and to have more than one option for getting a deal done. 

As always, any advice is appreciated along with any constructive criticism.

If you really like them, have a critical conversation for how you would like an issue like this handled in the future and put it into writing.

I just know the time investment that rehabs and new construction take and the criticality of eyeballs on what's happening. 

We called the police and got the report, my tenant was shocked had to take sick days off work due to insomnia caused by stress and loud music.

If you're a single mom with student loans, a car payment, and living paycheck-to-paycheck, then $20,000 would be devastating and a reserve is critical.

Leverage is critical because it magnifies either your gains or losses - it's really a question of your confidence in the deal, your ability to execute, and your tolerance for risk.