Sell Connecticut multi or Florida Air Bnb

[David Ahearn]

Hey y’all my name is Dave and I’ve been a follower of bigger pockets for sometime. I have 5 flips and 2 buy and hold properties under my belt. I have no cash at the moment and want to liquidate to do another flip, should I sell Fairfield County CT 3 family, or 2 bedroom 1 bath with a pool in Hollywood, FL? I have about 150k equity in the CT home and it brings in around 1500/mo after piti and expenses (2% interest rate, owe 400k). My Florida home has about 330k equity and currently makes about 500/mo after expenses (3% interest rate, owe 250k). I may be able to get the Florida home to 1500/mo or so if I rent it as an Airbnb (currently mo to mo $3,300, has a fenced pool, 7 min from the beach), and I’m emotionally tied to the Florida home as I bought the home for my mother who sadly passed away in it from cancer last year. It has so far double in appreciation from the CT home in about the same amount of time. 

I feel on paper I should sell the Florida home, and the only thing logically I can come up with to keep it is the faster appreciation of a south florida home vs a Fairfield county home in CT. They are around the same price at the moment. My income/credit is too low to tap any equity in the Florida home via heloc. I will be hard money flipping as soon as I sell one of the homes.

Do any of y’all have any experience or insight between the two markets, and what would you do? I could also keep both and just not flip for 2-3 years while I save money from my job. My ultimate goal is to get into brrrring in a state that is conducive for it Please let me know what y’all think, and thank you!

Dave