In addition to property sourcing, I require an agent who can negotiate effectively on my behalf, ensuring I secure the best possible deals.If you have experience in identifying distressed properties or working with real estate investors in Florida, I would love to connect.

.• Retirement communities• Syndicates (from initial explorations, little transparency from providers, little oversight - almost leap of faith and trust in provider?)

Then, if you are not satisfied with what you find, you can explore other options, but for now, I would find out what is happening on the ground face to face.Best of luck - Chris

Section 8 would tend to carry higher repair and as a result, additional vacancy.OP’s definition of cash flow is rent minus piti.  

Quote from @Victor Yang:In addition, is it possible for me and my wife to gift 36k worth of equity per year of the house (under the annual exclusion limit) and therefore have none of the costs go towards the lifetime gift limit?

It was held by the previous owner for a very long time, so I wouldn't be surprised if some basic facts about the house are incorrect.I was making an offer on a house a couple years ago and discovered that the owner was paying taxes on an additional house that was on the neighbors lot and didn't know it!

Stock market returns have been good and I don’t have the headaches of dealing with any additional houses or guests.

This would buy time to improve cash flow or explore better refinancing options.Ask Your Lender: Would they consider lowering the rate temporarily or extending the loan period while you stabilize cash flow?

If you have equity and decent credit, a conventional Fannie Mae HomeStyle (or the Freddie Mac version) would likely be the better option instead of an FHA 203k loan (which will require a 3rd party HUD consultant to oversee the deal in addition to having the contractor involved). 

Great use of space and provides additional income to offset the monthly payment.Orlando, and many other cities, have a "missing middle" problem in regards to housing.