Yes and no.
Reasons No:
This is a different situation than 2008 for a couple reasons. 1.) banks haven’t been giving out loans to just anyone, and 2.) a lot of the purchases occurring recently are cash sales. People are selling/cashing out equity in high cost of living area and moving it to lower. Also I think Floridas economy is in a fairly strong position all covid policies considered.
Reasons yes:
1.) The increase in prices has made housing unaffordable for many residents because wages haven’t increased at an equally rapid rate. This situation is generally going to be unsustainable so it could be resolved in a couple ways. We could see a dip in housing prices (not a crash, but a dip) that opens up the market to buyers who previously couldn’t afford it. It’s also possible that rather than fall, prices stagnate and we see no/low appreciation until wages catch back up with cost of living.
2.) Another reason Florida in particular is at risk for a crash is the large proportion of 2nd/vacation rentals. If the economy were to enter a deep recession, one of the first expenses people might cut could be that extra house they only use 1-4 months out of the year.
So is it the right time? No one can tell for certain. If you’re evaluating your investment properties correctly, it shouldn’t matter. If the numbers for a deal make sense, they make sense. Assuming you’re doing buy and hold investing a bubble won’t matter if you cash flow projections and buffers are good. In most of the country properties had recovered from their ‘08 drops by 2011-12. So if you know you can afford the payments and you plan on holding for 10, 20, 30 years, does it matter if values drop in years 2-5?
Hope you found this helpful. Ultimately it boils down to you, your goals, and what you consider tolerable. Good or bad market timing is almost exclusively based on luck and we’re often better off is we stop thinking we can control it.