I can certainly handle the bookings and standard service things, but the challenge right now is finding a cleaner who isn’t so expensive. 

Are there specific zoning or structural challenges in Florida I should be aware of?

To say the past few months since the storms hit have been challenging would be an understatement.

Our biggest challenge is that we are not over 55+ and we would prefer to invest our money in the villages itself.

Every state has their own real estate laws of course, so legal compliance will also be challenging.

If you are struggling to make the numbers work, then it is likely not a deal to pursue.Our biggest challenge in the New Orleans area is the cost of insurance.

You could look at “FIG” (fourplex investment group) I get ads from them occasionally. 

That's the challenge with doing a 1031 with multiple properties.

While running a large group of small landlords in Philly, i have visibility into the full realm of challenges that new investors face - and some are quite overwhelming and totally unexpected because they jumped in without fully understanding what they jumped into. 

I occasionally will get one and restore it as a labor of love, but they are all in very rough shape.