Now that the value has increased $500k, any additional increase will be taxable income when I do sell.

A 10-15 year payback very well might be a MUCH better investment than you are making it sound like because the price of energy goes UP in addition to the lifespan of the system being longer than you suggested. 

In addition to doing regular inspections as soon as someone gives notice due and immediate inspection to determine if the unit is being kept up decent or if you need to plan on some repairs before it is turned.

Many of these companies will provide information about the property, including the name of the owner, address, loan amount owed, and additional loans outstanding.

Additionally, make sure the deal itself is strong.Best regards, Stevan

If someone wants to host MTR, STR, whatever, they should start their own management company, not try to use this model where they can make additional money off of an owner if a property performs well.

. $150 plus tax Clean up fee at check out and $22 plus tax per day resort feePRIVATE OWNERS: $100 per day resort fee up to 2 people, $50 each additional person.

Therefore it's quite normal for a design change to be an additional service fee. 

Additionally the suburbs have higher taxes compared to Chicago proper.  

Is it to build up assets, is it to make additional income, is it to reduce your monthly housing spend and save more money, is it tax breaks/benefits?