I would use electronic combination entry locks and then you can change code whenever someone leaves. shared job chart or mom and dad you pay daughter management fee to cover cleaning, and managing property, grass, snow.. and that's deductible property expense.. 

This forced double-check mechanism actually prevents about 95% of what would-have-been a software or data entry errors screwing with someone's deal.- Minimal busy work, minimal compatibility issues.

Moderate entry point ($50-75k should get you a solid house), good rents ($1000+), and close to downtown Chicago. 

I am interested in entry level multi-family housing as well as house flipping. 

He is a perfect renter otherwise, pays like a clockwork etc, and the annual agreement was just renewed.So the first question is how to enforce the entry for appraisal, without going to court etc.And the second question - what is the best place to find a (conventional) lender who will take tax value in lieu of appraisal...Any comments are appreciated.

Consider looking at an entry level property management job for some practical experience. 

@Chris Soignier Well minus the condescension of calling me irrational, unsophisticated and providing me the Wikipedia entry of sunk cost, I understand your point, but I don't think you understand mine. 

RE is a very fractured industry.. with all different levels of bar's to entry..

What's your entry strategy?  

Depends on what you pick up but lower entry price is always a better environment for buy and hold investors.