We currently have a rental in CO that we are planning on selling when the lease is up this summer. We live in VA, and it's starting to turn into a money pit, the ROI on it was never great but it was on a 15 year mortgage so it was profitable for a small part. We are looking at buying a rental in the FL keys, possibly Marathon area. However, I am not familiar with how weekly rentals work. The numbers for down there (based on VRBO) show that if we can keep it rented for fair market value for 3-4 months out of the year, our entire mortgage would be covered for the year but does anyone have any experience with that area or with weeklies in general that could offer some advice?
Some background. Net worth is about 725k, including equity in rental and main houses of 200k, the 100k from the rental would be used to purchase the vacation home, no debt outside the two mortgages. We could currently cover both mortgage payments with monthly cash flow if needed. We do plan on retiring to the Keys in 7-10 years so we are looking at this as a jump start on building equity in a place we actually want to live in.
Anyone have any tips, tricks, or advise?