One of the best ways to get good information is to call local General Contractors to ask for referrals or City Building Inspectors. 

Your building Inspector may provide with any problems during your due diligence period. 

Are there any qualities that would preclude the inspector from considering it a full bedroom (closet, private entry door, etc.)?

I have identified an attorney to help me with wholesales, but I still need to find an inspector to help me out.With the help of BP, reading and reading some more. 

Have you looked to see what the terms of the lease are and are you allow to use a home inspector to verify any immediate repairs?  

I think if upvotes are an indication of credibility then that's who I'll looking for as a lender or syndicator, or home inspector etc.And @Mindy Jensen, don't you worry bout the 12000 to 900 ratio. 

10 roofs 10 tax bills 10 insurance policies 10 wet basements 10 closing costs 10 clogged gutters 10 city code inspectors 10 yards to mow .. the list is endless .

If you buy a 4-Plex and decided  to pull a permit for one Unit to start your renovation project and not the other 3 can the building inspector (plumbing, electric) mandate that you show the other 3 units during the first unit inspection ? 

Good point on the temp Bryan, glad to have a contractor in on the discussion.As far as the boiler condition, it's in the basement which gets fairly humid, inspector just made mention that some of the control panel, circuitry, components, etc look rusted and should be serviced as a precaution.

Hello.I'm in the process of purchasing an older 3 unit building in South Chicago and the inspector said the roof is at the end of it's life and it could cost about $20K to replace it.