I'm also an agent so I could easily throw it on the MLS and cash out the equity whenever I'm ready as well.

So may any seller.Using WCs can be spotted easily in an offer, you may have to justify what may not be customary.

Should I do a raised bar or counter height seating?

Aloha Account Closed who are looking to get past the 'bar to entry' in a market like this.I do partner with novices on occasion, and while I wouldn't necessarily 'feed deals' to a beginner, I would certainly let them jump in the back, fasten their seat belts, and hang on for the ride.

It may make it harder for others to know who owns the door, but that too can be exposed easily by a judge, I just never had to hide out in business.

It doesn't look like that one could be easily fixed and it also doesn't look very secure (even with a lock).  

Box fee and etc - which could easily bump up to $2000 a year.

If your neighborhood can support $200k condos, you can house hack this into a nice profit a few years down the road.The scenario I'm proposing:Purchase 285kRehab to HGTV level property 45k (total: 330k)Sell other condo for 220k - 15k closing costs = 205 (125k)Refi 4k (129k)Assuming value is still 180k (not HGTV level rehab) you could mortgage 160k fairly easily.  

They cannot copy it (well, not easily) and if they move out, you can deactivate their card.

I do think you're getting discouraged too easily though.