I'm leaning towards selling before I need to dump a bunch of money into the property, but I'm second guessing myself because I'm sitting at a 3.25% interest rate and cash flowing close to $1,000/month before reserves. 

Do I raise the rent and make $600 a month on passive income, keep the property and chance this home not appreciating much more bc of what's currently happening in Florida with excess amount of inventory sitting there?

I recommend you sit down and crunch the numbers with both scenarios,  and make an informed decision.

It's an education process.When you sit with the new lessees to sign, go over all of this so they understand the process.

If you have 4 offers sitting there, I would really start looking at them and weigh that with your motivation for selling. 

Great buy and hold area only if you let the cash sit in the property.

I did it for almost 5 years with minimal issues back in 2010's. It's

For me, I always have goals when I sit down each year and the fact is that it really takes me an extra 2-3x to get the those goals than I really thought.

Sits on a 0.44 acre lot.

Doesn't mean all condo buildings are great, probably 10% are sitting nicely right now and you have to find out which ones are.My major recommendation is get insurance quotes first.