Do you want to manage a possible weak cash flowing property from across country in two years (or are you going to get a great deal and sell it...counting on appreciation is not a great deal)?

I ran cross country and track at The University of Mobile and Mississippi State, so I know what it means to put in the time and effort to get what you want. 

What other prices must I also count when paying for a property?

Example:$1,000/month in rent counts as $750/month in cash flow.If the new mortgage payment is $750, it’s a wash.

So, make your first purchase count!

He doesn't seemed concerned about having the money secured; however, I just want to make him feel as comfortable as possible and dot all my i's and cross all my t's.  

Im unsure as to whether I should add as income what I would pay if I were a tenant or if I should only count the other unit as income and not mine.

I do for two reasons: needed to do it to increase mail count to a count I wanted and secondly, those are regular people going through the same stuff as non-trust people and may need/want to sell at some point.

I found rates and terms were much better when I used a local bank (specifically a bank that operates on the island).I certainly agree with establishing an LLC to conduct business but you'll want to be careful how you operate so your day-to-day activities don't cross between multiple companies and deteriorate the value of the LLC.  

People who look for legal advice on the internet are a distinct group, they are a cross section of not having a lot of experience with real-estate and do not want to pay for a lawyer.