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

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

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

I'm always trying to create content that will help people make more money, and start driving towards their soul purpose.Thanks for taking the time to read this and to share your thoughts.I believe People With Financial Intelligence Can Change The World For The Better".

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 recent economic report by Tatiana Bailey stated that over 10,000 new residents flow into El Paso County every year which is constantly driving up demand in the area. 

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