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

Is that "marketing" too?

The seller was a foreign landlord who was behind on a few years of taxes, and the property was in C5 condition at the time of initial appraisal.

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.

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. 

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Pre-understanding of the area/market, willingness to fix and live in an outdated and damaged home.

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