Paul,You typically pay 1 full year of home owners upfront (to the insurance company) than on top of that you will escrow between 3 to 5 months of taxes and insurance upfront.You mentioned flood insurance as well so first year  would need to be paid in full prior to closing to provide evidence the insurance has been bound.

I am retired military and I know the American Legion and VFW is typically quick to help veterans.

Local banks are usually more flexible, but they typically have higher rates and fees.

Commercial brokers typically do not have time to be bombarded by questions when in a transaction just so someone not buying can get (trained up).Reminds me of a car audio business sign I saw one time hanging in the front door decades ago.

Typically if you buy non-owner occupied and the property is vacant at the time of the purchase, the lender will get a rental comp. analysis as part of the appraisal. 

A typical portfolio is plus or minus 700 doors.

They sent me cabinets that were in different boxes, different construction, door sizes were off a half an inch, a pinstripe was a different color, they couldn't fulfill the order with the cabinets I ordered so they gave me different cabinets and said that they would work?

Hardship and grandfather provisions are typically included in a rental restriction, so monitor the discussion and proposed language, should your board contemplate the restriction.

I'd suggest renting out the basement, but seeing that you're likely in Florida, basements aren't typically available.I used to rent out rooms in my house, and it worked out fine and decreased my PITI mortgage by half.

I've found that the typical response rate to direct mail marketing had declined like crazy.