One of them raises the dues frequently, cutting further into my cash flow. 

Not impossible, but the odds are stacked against you and often you are competing with extremely well qualified and experienced investors.I've been hearing for years that people have been just killing it in the short term rental space, but I'm a conservative investor at heart and while revenue is frequently higher, there are many additional expenses and often an exceptional amount of volatility just inherent with short duration stays. 

But I am very concerned that Florida gets frequent floods and hurricanes which ends up in huge property damages. 

It's hard to know where to start, but we enjoy going to STL, and know a LOT of people in IL who travel there frequently for Cardinal games, etc....so it seems a logical place for us to begin investing. 

A casino is coming to our town, I already bought a quirky round house and a triplex to do medium and short term stays.My daughter has a thriving flower business in the shop downtown.  

The tankless water heater is used much more frequently in Socialist places like Europe than America.

One market may perform well while another does not.What I feel is a more accurate assessment is the following:Prices of properties in locations with solid fundamentals before COVID will likely have minimal, short-term decreases.Prices of properties in locations without solid fundamentals before COVID will have significant. and long-lasting price decreases.Locations with solid fundamentals met all the following criteria before COVID (2020).Prices and rents rose faster than inflationBoth state and metro populations were increasingLow crime rateNew companies frequently moved into the area setting up operations and creating jobs.Operating costs were low.

As was previously mentioned, you run your business.I have a couple of Realtors that I use frequently, because they listen carefully and follow my direction.

How frequently?

This can help you save money by avoiding penalties and maximizing your deductions.Keep up with changing tax laws: Tax laws related to real estate investments can change frequently.