I know a dependable PM would get a tenant out ASAP if they werent paying rent or causing trouble where as an owner could easily let things go for longer because they dont know the steps or feel bad.

Do you really mean to tell me that just cause the calculator says `17% CCR you'd do the deal?!?!

You know why - cause you can't express yourself clearly.  

May cause the tenant to back down once he realizes it's not going to be an easy payday for him. 

In this scenario, since it seems the primary cause of concern rests on my shoulders, how would you fine folks present the deal?

Even mechanic liens for roofs or any materials that once removed would cause damage to the structure are wiped out in foreclosure... not a lawyer, but have some experience here.

You may have had $170K in appreciation the last few years, but how much of that appreciation was just digging yourself out from the market crash that caused you to go underwater in the first place?

Now, we need to look at the law.First, pursuant RLTO Section 5-12-140(a), no Chicago rental agreement may provide that the landlord or tenant agrees to waive or forego rights, remedies or obligations provided under this chapter.Second, pursuant to Chicago RLTO Section 5-12-080(d), deductions may be made to a Chicago tenant’s security deposit for only two (2) things: (1) any unpaid rent which has not been validly withheld or deducted pursuant to state or federal law or local ordinance ; (2) a reasonable amount necessary to repair any damages caused to the premises, reasonable wear and tear excluded.Based on a clear reading of RLTO Sections 5-12-080(d)(1) and (2), a Chicago landlord has the right to use a security deposit for unpaid rent and the tenant has that same right.

Financing it (and causing problems with current lender) are a huge pain and even insuring it is difficult.  

This can cause some installation issues when running the wall cabinets to the ceiling.