Describing his duties and his form of payment.

So you would have to buy two of the remaining units to get over 60%.From what you describe unless you are in a high demand location the size/condition of those other units suggest you might be able to make a fair market offer that might not break the bank  (knowing nothing about your own finances of course) especially since the housing market has slowed down a bit right now in seattle,  though of course some areas and segments are more affected than others.How much do you know about the other owners?   

Sounds like he is kind of financially strained the way you described the situation.

If you start buying and stay in the market like @Christian Montalvo describes, then you will start to find the "unicorns" that are good appreciation and good cashflow.

I am hearing lots of people who are self described professionals in the business saying that current owner searches are enough.

Not applicable in the situation you described.

There is one company called Nordic that has something like you describe I think in Pattaya, Phuket, and Koh Samui.   

Most houses have pics in the bedrooms that would get me banned again from Bigger Pockets if I described them.

Known problems are:Sewage pipe needs to be snaked every 6 months, might need a new systemThe existing tenant was described as a "pain in the ***".

I seem to have more issues with guests that try and negotiate as @Mike V. mentioned as well as last minute bookings as you describe.