The property is in Joseph Lee and in the 250k range (but it is a duplex) The PM is downright awful.

My main concern about actual house hacking for a few years in a row is that we don't want the kiddos to have to change schools once we relocate up there.I'm thinking about getting an appreciation-oriented duplex/triplex in a pricier market with good schools that we could stay in for several years, and saving for an actual cashflow property that'd we buy as an investment property instead of a house hack.

This was a no money down deal was a tri-plex, duplex, SFR and studio all on a few city lots.

This would be like comping a SFH to a condo where you cannot rent the condo, you pay to rent the land for the condo, and you may need to move the condo unit. 

Over the summer I used a VA loan to purchase a 3br/1b per unit duplex that I'm currently house-hacking, doing a live-in remodel on the second floor with the first floor totally updated and occupied with college students.

I successfully operate a small portfolio (3 duplexes and three single families) out of state and a good  property manager is essential. 

Unless its condo, co-op, or HOA you should be fine.

Look for fixer condos.

I am attempting to purchase a triplex and a duplex on a single 2.5 acre parcel.

When I was stationed in Northern VA, high costs had me stuck until I sold my Corvette to meet my DTI ratio and get a condo using my VA Jumbo LOan—one of my best investments.