Hey Sean,
If you can dump the condo without a loss, I'd bail on it. I've had two since 2005 and am just now at a break-even point for a sale. Between the ever-increasing HOAs, competition to keep them rented and updating I'm only generating a 4% Cap. Since your's is a single bedroom, my experience between the two that I own is the single bedroom gets a lot less traffic and has had more down-time than the multi-bed/bath.
Your plan to live in one of the units in a MFH is genius, if your situation permits. However, I would still advise finding the best deal possible in terms of Cap Rate, appreciation prospects and rental traffic for starters. You'll also want to understand the area, especially the type of tenants/demographics for your market. Since you're living there the type of tenants can/will have a dramatic impact on your quality of life...
On another note, everyone wants to "pay down debt"...which is great...but if you can carry the debt at a lower interest (say 4%) while putting the funds you'd use to pay it off into a higher interest earning scenario (say 7%-8%) it doesn't make good fiscal sense to pay it off. So run the numbers and figure out the best approach for employing your available funds.
If you have any access to financial advisers at work, e.g. 401k Managers, etc. I'd strongly advise asking them for advice or referrals to folks that can review your situation. You'll have to suffer through some pitches, but you'll get some insight into personal finance strategies that you can research and cross-reference. Building wealth takes time for most of us...good luck.