Great tenant but property tax increases have reduced my cash flow.

There are rental management tools like Stessa, Baselane, Innago, and many others that include income/expense tracking that handles all the accounting tasks and reporting you really need for rentals. 

Hi Ben, doing this for 20 years, I’d say if you move forward, refinance your two rentals to the max they can handle under a stress test for mortgage payments.

How to handle the requests in a timely manner while keeping expense down.

Turnkey companies usually handle buying and renovating the property, then partner with a local third-party management company to handle day-to-day operations.

I 100% agree with everything JD said, as his approach is exactly how I handle clogged pipes for all of my rental properties. 

Again, a buyer's agent working for you would handle all of this nonsense.

They'll likely have follow up questions about who handles maintenance, larger SD, etc... so be prepared to quickly answer these.Value to mention:- Professionally cleaned property after each stay and exterior upkeep- Staged photos that you can share with the owner for marketing purposes- Capex coverage up to $XX,000 (might need to include in SD)- Extra $XXX per month (likely may need to pay a little extra in rent to make it worthwhile, otherwise they can collect the same amount as LTR)Also, google "Airbnb apartments" or check their website. 

Or else reduce enough on price to deal with an eviction from an illegal unit.I don't know Chicago laws, but in NYC if you have an illegal unit, the tenant occupying it seems to have more rights than the owner does and doesn't have to pay rent... 

And make sure you have the financial resources to handle that.