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.

Back when I was brokering commercial real estate 100 years ago I had a deal on a small office building fall through when during the walk thru just prior to closing the buyer insisted on checking the candy vending machine and verbally to;d us and sent us a follow up letter informing us that he wasn’t going to close because the Baby Ruth’s in the candy machine were stale.  

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?

I purchased a duplex with 2 sets of tenants just like yours last July. after going thru the process with the first ones and paying a flat rate, I was able to negotiate A split rate for first the filing and then the court appearance.

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.