If your property management company is good and has built an internal maintenance team which has set rates and had strong relationship relationships with licensed contractor which should keep costs in control, you should never need to shop contractors on your own I wouldn't think.So in short, our policy is give us your preferred contractors upfront if you have them, but then we work all tickets to resolution including dispatch, and payment of invoices.This is of course for operational expenses.  

Pretty sure they will have it covered in their PM contract.Their PM contract also probably allows them to set rental prices.

Cash flow in the triangle takes creativity, just want to set that expectation with you.

I never liked Airbnb's or VRBO's pricing structure because it seemed more like they set a price that will get you booked so they can get paid, and not necessarily for the profitability of your listing.

I would also look at your skill sets and go from there.

It is also possible that either the folks in charge of the station, or the prosecutor have set a policy of not wanting to pursue non violent crimes, or even not paying attention to crimes against folks who are not local residents. 

Typically, we set up entities in the state in which the property resides.

I would like to do some research on other rental properties before I set my priceComputer algorithms are good for studying a general market, maybe even a neighborhood, but they are terrible for evaluating a specific rental.

Planning for flexibility with frequent moves and understanding property management will set you up for success when you start investing in 2026.Good luck!

It’s humbing and frustrating, but it also teaches you those guardrails you’ll want next time.. like thorough screening, a solid lease agreement that sets ground rules upfront, and maybe even setting aside a bit more cushion in reserves.Chicago’s got plenty of investor-friendly pockets.