I would first find a market that is showing signs of market growth.

Yes, the deposit is refundable only if we can not deliver free and clear marketable title.

Purchased off market for 180k, EST rehab 40k, EST sale price 279k.

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

So I took action, I know nothing, so I thought the fist step would be talking with an agent and get an idea of the market value, make numbers, and then look for options to finance the asset.

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. 

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).

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

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.