@Joe Splitrock @Jay Hinrichs agreed our cycles have moved longer than expected on this one due to unfeathered intervention by central banks, we are moving back into the non- bank underwriting more than 40% of new mortgages  from 10% in 2009.

That's an example but something in the middle ground that works for both of you.I'm a bit non-plussed with some of the large multi-family syndicators who like to talk about how they can force rents up for lower income people and in almost the same breath talk about how they help the same people with their charity...I think, like everything else there is a productive middle-ground where you can earn good returns and not force people into bad situations.

As you may recall, I have some tenants moving out that cooked extensive Indian food which tends to linger a bit more due to all the amazing yummy spices.Can you recommend a good carpet cleaner and maybe the same or se...

In these scenarios, I typically call the tenant and set up a meeting, and then in a very non-threatening way, just ask them what their current plans are as far as if they're hoping to renew at this point, or if they're looking to move soon.

Using non-rounded numbers is a common and effective negotiating tactic.

You can buy an investment property directly in your IRA (or IRA owned LLC), and if you wish to use financing you must use non-recourse loan. 

Just a thought, if they’re clean and everyone gets along, seems like a win win. 

How bout this, rather than sinking so much money into Dead Equity, look at paying off other NON tax deductible debt, invest it in retirement savings like a Roth IRA, Annuity, Loan the money out thru a company like Prosper or simply put that money in the bank and let it subsidize your monthly nut.   

Check for fraud in payments and distributions to non existent contractors.

It is worth considering areas like McKinley Park (right next to Bridgeport and also becoming a Western extension of Chinatown), West Pilsen (still seedy enough to yield an occasional good deal), or Bronzeville (again, pockets of dereliction open up the opportunity to help clean up your own little corner of the neighborhood).