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.

Let's not assume you must take a hit on your credit until we explore some options.  

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. 

I work with residential, commercial, and government, I never charged anyone for estimates, some take me plus an architect 3 days to complete.For the investors reading this, please note different contractors have different rules, regulations, and methods on how to run their business.

I have been doing it just over a year and that gave me little confidence to explore investing more.