Networking, networking, networking.I know... it can be awkward sometimes.

My experience is that staging helps especially when you have an awkward or undefined space/layout. 

If fixtures, plumbing and wiring have been stripped and/or the buildings have been left unheated during {part of} the past ~7years, there could be additional costs.As for the seven unit, whether you need to rehab is ultimately your call, but just looking a the small window provided by the pictures you posted, I would be planning to "freshen"/update the units and address some layout/usability awkwardness.

Plus, the "third world dictator" look (while awesome for some purposes) drew awkward attention when driving around el-cheapo neighborhoods looking at houses!

Some will say to not let the third person off the hook, but he's not staying and it will make for an awkward situation if you don't take the high road here. 

I dont want to contact my lawyer again because honestly, he always seems rushed and it just makes my conversations with him awkward. 

I personally prefer this approach, its simple and straght-forward, and you're not dealing with the awkwardness of taking application fees from numerous applicants.

I find it to be an awkward position.

I feel somewhat awkward when I am showing this property to people older then myself and asking them to show me proof of their income, etc.

Another thing, it is both non-traditional and also very awkward for her to be present in the condo during showings so if that's what she wants, I would explain to her that it can really weird buyers out when the tenant/owner is present during the showings.Unless you have authorization to show the condo until she arrives back in town, you'll probably be violating your state tenant/landlord laws, and if she absolutely won't budge, just wait the two, weeks.