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.

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

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

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.

I quickly learned to ask my sellers to leave a few minor things for inspectors to find as it drives me crazy that most will nit-pick a house apart if it’s in great shape and they can’t find much to report.