@Anita Kollory as far as returns, it all depends on what type of loan you'd be getting, your comfort level of buying locations, how much you're approved of, and several other factors.

So we all know a pool is generally regarded as a bad investment, and I might get back 25-50% of it's purchase price, but this is Florida and it's damn hot here, lol.So we have been looking and not finding a ton in our comfort range.

I would feel comfortable with a $100,000 duplex. 

If you are not comfortable with this aspect, your agent will help (not always the best resource).Due Diligence - The offer should contain a stated period of time during which you get to check things out.

If you intend to refinance in the future, then your contacts at a bank can offer some advice on what they would like to see to make the bank feel comfortable lending money. 

But it is the neighborhood we are most comfortable with and go back to visit, so we wanted to stick with something we know.

I recently took a course on how to properly estimate cost of repairs and rehabbing houses for profit, so i feel somewhat comfortable enough to do my first flip.

Remember there are variable expenses such as vacancy rates, repair rates and management fees so when someone tells you an ROI make sure your comparing apples to apples meaning create a formula you're comfortable with and then run all of your prospective properties through your equation.

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.  

That way you can give a copy of that to the seller with your offer to make them feel comfortable with you.