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. 

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.

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.

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?  

Pre-understanding of the area/market, willingness to fix and live in an outdated and damaged home.

My expertise lies in the vibrant market of Pinellas County, where I've honed my skills for over 7+ years.

@Karl KauperManayunk, East Falls, Roxborough, Fishtown, Northern Liberties, and University City are safe neighborhoods with diverse populations and strong rental markets.

Hopefully someone from that market will chime in and make it easy for you!