I have basically lived here all my life, I have been in the plumbing trade for over twenty years and if any one has a question about plumbing I will be happy to help, just give me a couple of days to reply.

Your crossing into unchartered waters in many a facet, and, although I follow the method to your madness, the deal sounds like a dog with fleas.

Craigslist is probably better because you can see what others are asking for similar properties in the area.But, in my opinion, the absolute best method to determine optimal rental price is historical data, which is only available on MLS.

This means that as of now my goals are very general: to learn more about RE investing, determine solid methods for purchasing without my own money (b/c I'm a poor college student), how to get my business off the ground, and wholesaling as a starting point. 

I just want to always be honing my method of calculating numbers because that is the hardest, most subjective and most critical part of the deal.Any advice would be appreciated.

If your roofer can tell that the pitched portion of the roof has 8 layers on it, I would think he should have been able to do the same for the flat portion using the same methods, unless this area had no exterior edges because of where it was positioned on the roof.

I am looking for any tips, methods, or other that may help me become skilled in the area of determining the ARV of a property. 

What is a "flip an hold" either someone has given a name to (an) old method(s) or you're getting things mixed up. 

This seems like a non-conventional method, but if they do the trick, I think it's an awesome idea.  

I don't think my current method of paying my handyman an $85 trip charge is cost effective.