I referred him to an estate lawyer but he still thinks he can get around having relinquish the proceeds of the sale!

I woukd definitely get a lawyer to look over everything for you before any action. 

From the tenants perspective, they'd probably like it and feel empowered to call and organize it, and I'd assume it'd be processed faster than the landlord or PM who might want to verify it.    

@Kelly Holly unfortunately i do not have a lot of experience getting stuff fron HOAs. my only suggestion is to read your bylaws very well, and if you can find anything specific that might point to their responsibility, quote it in a strongly worded letter. if necessary have a friend draft it or pay a lawyer to write it. if they still refuse you may have to pay an attorney to fight it for you, at which point it may be cheaper to fix yourself.

I've spoken to acquaintances who are RE lawyers and they don't have any experience in setting up a deal like this.

Btw, we live in MN and have read the renters rights there but they still don't answer this.I just emailed a lawyer too, so hope to hear from that person soon.

On one hand, I was told that I can hire a PM company in the area who can do everything on my behalf - go check on the property, and if there's someone there, take the necessary steps to get them out, whether it's starting the eviction process, or even offer them some money to move out.But I've also been told that I need to contact a lawyer first instead of a PM company, and I'd need a lawyer to do the eviction.

I would not describe Illinois as landlord friendly, it's not, but there isn't as much landlord-tenant related covered by state law as there are in some other states like California and some states out east, and parts of Canada.If this is your unincorporated McHenry property, unless something changed that county has no rules on rentals either that I am aware of.You may want to consult with a landlord tenant lawyer in our area for an hour and learn what you need to do for our area.

Anyone know any good CPA's and/or lawyers in SAN DIEGO to help evaluate the best legal entity formation for these purchases?  

Insurance companies have lawyers that work with claims all the time.