TL;DR: We are good at long term rentals, but we want a beach house. Is that a bad idea?

Background: My husband and I own a few (mostly local) long-term rentals that all have a positive cash flow. While I'm not finding the amazing numbers that some might find in other areas, I run very conservative numbers prior to purchase and usually get a better return than I anticipate. 

We know our own area well, and can almost always find deals that we'd like to pull the trigger on, but until we accumulate more cash, we can probably only purchase another $100-120k in property before we slow down and wait for our debt snowball to catch up (pay down the HELOC and eliminate the cheapest mortgage to open up standard financing options again).

Here is the conundrum: Another local long term rental (or two) would be a great decision, BUT a beach house sounds like a lot more fun.

Specifically, we are 2 hours away from Panama City Beach, and we are curious to get into a new type of real estate. We have the cash to get 1-2 places locally, or get a tiny beachfront studio that we could occasionally make use of. My husband would definitely want to use it once per month (even in winter) since he is a reservist in the coast guard there.

Do we boost our retirement fund by taking a more conservative approach at home, or do we get a property in PCB that allows us to pretend we're already retired for 2-4 days a month?

Considerations: 

- It's hard (maybe impossible?) to find a short term vacation rental property that will cash flow - especially of the small 350-700 sq. foot studios we can afford right now. (Any advice on this issue would be most helpful!)

- There are so many fees/costs and restrictions to consider. I am not excited about trying to accurately estimate the expenses or cash flow, but I am interested in becoming an expert in a new niche. (I've already begun work on spreadsheets, but finding out the specific fees and management rules for each condo/condotel is daunting and I don't want to start actually shopping until I know a lot more about each condo association).

- I am totally aware of the problems with condos. I plan to thoroughly vet each association, but there's only so much that you can do to ensure they stay on track.

- Use restrictions and potential profits during the busy season may prohibit us from getting the best use out of the place.

- Appreciation will likely be better on the beach. Or a hurricane will ruin it. There's really no way to know for sure.

- I may be too practical to let myself purchase a mediocre deal and I am not interested at all in a bad deal.

I realize this is an emotional and impulsive desire to have something flashy instead of another safer, practical rental, but I want to hear from you guys: Is it possible to find a cheap beachfront studio and make enough cash to consider it an investment, or would I just be throwing money away for a slightly brag-worthy deed?

Just FYI (as it may be helpful to someone out there), here is my list of questions for consideration regarding short term vacation rental condos:

What kind of short term rentals are allowed? (minimum/maximum nights, pets, etc.)

What kind of rental income does this unit generate?

What kind of rental income do other units similar to this one generate?

What kind of management does the association provide?

Are the rooms assigned rentals randomly or based on some sort of specified system?

Are we permitted to manage our own unit’s rentals?

What fees and restrictions does the condo assn impose on rentals?

Is there a maximum number of days of residency per month/year, etc?

Does the association provide water, electricity, high speed internet, cable, etc?

What kind of passes/permits/wristbands etc are required to access the amenities?

What kind of local regulations are there on short term rentals?

Has the association voted to waive funding of reserves at any time in the condo’s history?

Are the reserves fully funded currently?

Do the governing documents permit the association to waive funding of reserves?

Are there any special assessments in recent history or are any pending?

Are all advertised amenities in working order? (All pools are usable etc.)

What are the typical costs of utilities, property taxes, insurance and the cost of furnishing the property in a manner consistent with the rules? Who pays for damage to the furniture, missing dishes/utensils, etc.?

Are there rules for interior furnishings/decor?

What kind of preparations are provided by the management for storms/hurricanes?