I think a big missing piece from the puzzle is where are you at personally with your income. Equity and cash flow are equally important when deciding whether to pull money out.
If you can put the equity to work by adding another property while still having a nice cushion on your cash flow, then I would say definitely yes.
If you were to refinance property one and pull out another 100k (lets assume a 500k house in tampa that you need 100k for a down payment), you'd be paying 6.5% or so on that 100k. Now you have to see what your returns would be on a 500k str property there.
Lets say you were to net 5k a year in rental income, there's 5% right there. Add in the principal paydown on the investment property which would be another 5k. And now another 1k of principal paydown per year on the 100k additional money in the new loan. Now you're at 11% return. And then add in the typical appreciation of say 3 to 5% (of 500k). Another 20k? Now you're at 31% return.
Now thats making a couple of key assumptions - 1) the property you're buying is around 500k. And 2, that the property with 100k down will have a 400k mortgage and will net you 5k a year.
And that may not sound like much. But what does that look like in 10 years. That property might be making 15k to 20k a year in rental income. It might be worth 700k by then. And you would now owe about 330k by then so you would have gained 370k in equity in 10 years. All from taking out 100k on one of your properties.
The key, to me, when deciding to use more leverage for growth. First and foremost, is the property you're going to use the money to buy a good investment. And then the second item is - if you do take out more money, where does that leave you from a cashflow standpoint.
Again, you appear to have two long term rentals. If one of those people doesn't pay or they move out, you're taking a hefty hit on your cash flow for sure. Does your personal income give you enough of a cushion to handle that. If it does, then to me the answer is absolutely clear - take that money out and add more property.
You will thank yourself a million times over when you see what that choice becomes in another 10 years.
btw: I would add that I am very skeptical of anything in florida these days. I did some mobile home deals down there (4 total) and the change in immigration laws and the recurring storms has really dented the demand down there. Then again, as an STR I'm not sure that matters as much because you're not selling the home, you're renting to vacationers so that shouldn't be as affected. And the benefit to all the chaos with the last two storms Is you should be able to negotiate a killer deal on a purchase right now.
I would put in lowball offers (75 to 80% of list) on every house you're interested in and see if somebody bites. You're an investor. You should never pay retail! If you can walk into the deal with some nice equity then it gives you more options in case you want to get out of the area.