I also haven't found any title companies in Oregon that work with wholesalers or handle double closings—unless they’re nationwide companies, which I don't know much about.

Have a candid conversation about how he plans to handle representing both sides and ensure you’re protected with things like a solid inspection period and contingencies.

I would just a hire a good PM and let them handle everything.

Upshot to readers: Know your state laws and real estate commission rules and how your state handles similar cases.

Do you think it’s best to use them or can I handle these transactions on my own? 

Educate yourself on how to better handle each one of those issues, starting with the most immediate problems first.

It sounds like you’re handling this situation thoughtfully, and you're right to question the validity of the HOA’s stance.

Start doing category 1 items right away, provide notice and do category 2 as soon as you can and finally prepare and get ready to initiate category 3 items based on your ability to handle them. 

So, the first question they usually ask a PMC is about fees - instead of asking about services and HOW those services are executed.EXAMPLE: PMC states they will handle tenant screening – what does that specifically mean?

You have to handle the leads well.