If you are consistent with these action items you will avoid most claims, your business will be more profitable,  operate more efficiently and if a claim were to arise you will have all your ducks in a row. 

To avoid going through the same poor experience, keep reading.Even if someone gives you a referral here, do NOT make the mistake of assuming that the PMC will meet your expectations, just because they met the expectations of the referral source.In our experience, the #1 mistake owners make when selecting a Property Management Company (PMC) is ASSUMING instead of CONFIRMING.It's often a case of not doing enough research, as they don't know what they don't know!

North side: Avondale, west logan square, albany park, rogers parkSouth side: Bronzeville, brighton park, mckinley park, bridgeport, west half of pilsenI agree with “trend is your friend” and avoid areas that might but havnt popped off.

As mentioned elsewhere, as much as you're able to do so now, handle all estate matters so you can avoid probate.

Then you can avoid the self promotion issue. 

This is correct, so I would disclose every aspect of the sub to and how it relates to the seller, perhaps going so far as to insisting the seller sign off on an acknowledgment that he understands the ramifications.  

Consider the "2 of the last 5 year rule" to avoid capital gains. 

I like the all-in-one aspects a lot.

Yes -- Nobody should try this unless all aspects are managed as needed. 

Also make sure to consider all the aspects you can including the tax differences.