I'm very fresh to the whole real estate world in practice, I'm trying to gain some experience of any kind.

Not through Fannie Mae, but there is a whole tier of lenders out there that can do that loan. 

I've spent this whole winter in Oahu and absolutely love the island!

It would be closer to home ownership without the whole burden of exterior maintenance. 

My whole business is online currently, and over the last 5 years, I feel isolated.

For example, 100k house you need to buy for 70k all in, which means that you need to get that house for 70k - Rehab cost (get to know a good contract with a middle of the road price point so that you are not telling people you can do a whole house for 5 grand) and then subtract the fee that you want to make on the house and that should be the target.

That is a whole nother question.

It's a whole new world of information.

My builder is willing to bring $200k to the table, although I'd prefer to finance the whole project myself if possible.

If you view it as the whole pie by paying off mortgages you are not seeing the entire financial picture and definatly not using your investments to the greatest advantage.