I'm patient, and I know this is going to take over a year, but the cost of entry is painfully cheap, that's the only reason I'm considering this.

Basically I'm trying to examine if there are any inefficiencies/pains in the *** that can be automated away to save hassle and headache.

As I mentioned initially a lot of people on BP are anti-condo, so it simply means you'll have fewer fellow investors competing with you.HOAs can be a pain in the neck, and condo associations are more invasive.

My guess is that numbers will be irrelevant until she feels the pain.

That's the time to remind them of their pain points and tell them why you're offering what you are. 

Thanks again  If you don't make it your primary, then your spouse does or it has to be like 100 miles from your duty station w/ intent to retire in it.But also just another FYI, both FHA and VA are huge pains for the buyer/seller.

What are the benefits - and pains - of landlords renting out a property individually by room (not as Airbnb)?

I'd give him the legal notice, and return his deposit (yes, it will be painful, but if you don't have proof, IMO it's a lost cause, not worth the hassle/stress) , and offer him a sliding scale, $400 if he moves out next week, $300 if he moves out in 2 weeks, $200 if 3 weeks, contingent that he cleans up the place too.  

For cheap money I’ll go through some pain.

It was a domino effect - slow an painful for the property owner when the deal goes south.