As far as the market, I would not make your decision on timing the market.

I've operated MTRs in several markets and have seen 75-80% occupancy on MTRs that can't be rented as STRs due to regulations (ie we don't rent them as a hybrid MTR / STR strategy).

My other option to house hack is Pittsburgh as I have family there but the property taxes are insane and it seems like the room rental market is very college oriented (I could be wrong.)I'd appreciate any feedback on Hagerstown and househacking. 

The bottom line here is that the State of South Carolina has decided that if someone wishes to advertise or market a property that they have no LEGAL interest in, he has to be a licensed RE agent.

June 2024 Lee County Florida Foreclosure ReportThe June 2024 Lee County Foreclosure Report was complied by Jeff Tumbarello, Director SWFL REIA , Broker/Owner Steelbridge Realty LLC Principal , Venture Investment PartnersThis is my work, done for me and shared with youThe data in the report came from multiple sources.Those sources are:The Lee County Clerk of Court, and MLS data (from my membership as the Broker of Steelbridge Realty LLC)We haven’t published this report in a while as the market trajectory previously rendered this dataset less crucial for forward-looking decisions.

Best wishes fellow Florida agent :)

I feel like a gambler who got pretty lucky in Austin and I would like to get out of there while I'm ahead, as it is still a correcting market and houses are quite expensive.

Pre-understanding of the area/market, willingness to fix and live in an outdated and damaged home.

If you have the money, and are asking the question, I would say you are ready.The only other question might be - are you timing the market right?  

Goto some networking events in your market and see about teaming up with local investors on your first one.