What concerns me more than anything else, is management's complete refusal to share the pain with their investors.

Painful.

I will never do anything in the city of portland again.. its just too painful... 

I pushed back every time and he ended up always paying on time but he was such a pain and always tried something every single Rent Day.

This has been a pain since day 1 - I acquired this property and this is tenant the previous owner had (without having any due diligence).

Figure out who the interested parties are; help them open an estate and get appointed as Administrator / Personal Representative / Executor; and then sign a purchase and sale agreement with them.Point being the decedent's estate owns the property and that's who you will need to deal with if you want to buy it.

E.g. roof replacement is a major pain when 2 people need to agree.

It's just painful to spend more when I'm already paying rent in full myself and the tenant has done extensive damage over the years so every penny I can save is very important.

Again, where is the legal or tax advantage for entering into this transaction structure, which will complicate your tax returns and add to administrative overhead?"

But I totally feel ur pain.