It’s been driving me crazy! 

It Depends.Potentially capital investments in the properties could have accelerated depreciation benefits (carpet, LVT, trim, appliances), while also allowing you to drive higher rents, thus saving on some taxes in the short run while driving increased values. 

I'm betting on demand increasing when rates go back down, which will only drive prices upward. 

I'm also looking at Sacramento since it's within driving distance but prices are a little more challenging.

circumstances.. education.. personality .. innate abilities.. lack of understanding basic math..desire .. drive.. familial pressures..  

Only  3 hr drive from Chicago, and totally worth it.

Have you considered Indian Rocks Beach, Largo, or any unincorporated cities that are a short drive to the beaches?

Apologies if this drifted from the topic of the original post but I think Joe’s question drives to the reason that I don’t have an easy way to slowly build up the experience that I asked about initially. 

Mine currently allows weekly rentals but it's driving insurance costs high.  

A lot of time, younger folks who can drive are great gophers (go for) for investors, picking up permits, etc.