So long as you can keep it occupied and drive up your base rent over time, your property will appreciate and you will maintain (and increase) your equity. 

Mainly looking into flipping some houses and also small multifamily properties as long term rentals. 

I'll be 45 next month.option A) Kiyosaki Model: Don't sell and run either long term or short term rentals through it for a year to show income on the property than pull a $300k mortgage on it to build another house in the same neighborhood... repeatoption B)  Ramsey Model, Sell it for $600k.

You should look at AirDNA for information about short term rental in the area.

They have higher appreciation, better tenants and great long term wise.

The high HOA fee is already a factor, so ensure you’re comfortable with the overall carrying costs.Focus on the Land Value: Since the lot has development potential, you’re looking at this as a long-term investment.

Make sure that your area states it directly.Otherwise, let the booking site handle things. 28 days isn't that long IMHO depending on the area or reason for traveling. 

Quote from @Jimmy Sont: I'm looking to build around 700 sq ft 2 bed / 2 bath guest house primarily used for short to mid term rentals.

Florida, particularly Tampa and Central Florida, is a strong option because of steady demand, landlord-friendly laws, and solid appreciation.If you’re debating between short-term and long-term rentals, I’d say long-term rentals are more stable, especially with the recent saturation of Airbnbs.

The fact that you evaluated whether to sell or do a cash-out refi shows you’re playing a long game and keeping your options open.