Once you have built a solid understanding, know how to wholesale, and have multiple deals under your belt then branch off and do your own thing. 

I understand.

Since they'll have full tenant rights, you need a solid lease agreement.

there are nice neighborhoods in Pittsburgh where you can buy a solid, older SFH in the 200s and no one is building SFHs for less than 2x that.

You should also look into getting your own bid.This will take some work on your part or you MUST understand that you will pay someone for saving you time.

This is a two-way interview, so have a short list of questions to ask the mentor (What books do you recommend I read to gain a better understanding?

I am getting very close to understanding it.

I 100% understand that state, county within state, building type, age, depth of coverage, etc., etc., etc. is going to make every property unique, but it would be great to come up with a rough rule of thumb that will allow a conservative estimate.

Within the city limits, I believe STR are prohibited, so start with understanding the regulatory environment. 

The thing is to sell conventionally - potential buyers understandably would complain about the Ticky-Tacky stuff.