It's a pretty extensive rehab with complete sub floor replacement, likely roof replacement and reconfiguration of the 2nd unit since overall layout is really awkward for the 2nd unit.  

A Realtor might be more friendly and helpful but again it makes me feel awkward in the situation.

If it wasn't awkward, there probably wouldn't be as many deals, I guess.

Forced-air gas does let you have central A/C if you want it... maybe that lets you get rid of a window unit that's in an awkward spot or noisy or whatever.In 2009 there were some federal tax rebates for more efficient HVAC (or more insulation, better windows, etc) but I don't know if those are still available... the furnace salesman should know all about them. 

I've had to make this call many times, it's awkward but it usually only lasts a moment.

And thanks for the flashback to my awkward junior high dance days!

Besides the liability ramifications, things can (and probably will) get awkward quickly when the job is done wrong, or rent is late. 

Of course, I also like to preface it with prior communications if possible (because it really can make the next 6 mos awkward) but they seem to not regard the landlord-tenant relationship with respect by their repeat behavior, and  it sounds like you have exhausted this line of rational, patient and understanding communication. 

Greetings all,I am in the awkward position of filling a couple of vacancies on my team after my first purchase...

You need a signed lease with deposit and all that jazz, which is kind of awkward to arrange if you're still living in the place and not moving out for over a month.