Make sure you understand the local rental market and have a reliable team for rehabbing properties.- **House Hacking:** This can be a great way to start, especially if you're looking to live in one of the units.

@Michael Almand, for a full line-by-line breakdown and scope of work, my preferred contractor will charge about $250 to walk the property but will credit it back if he and his team are given the job.

Getting the system/team in place will be key once you start to scale with STR in your market.

If you go that route, having a solid team (property manager, agent, contractor) is very important.

@Jacob Dalton, I'm going to have to agree with Jonathan Klemm (sorry, couldn't tag you) & @Brie Schmidt -- you can definitely be a successful landlord in Chicago with the right team in place.  1000's of investors do it every day. 

A million dollar sell order wouldn't move the price much at all. 

Hi Mike-Congratulations on being a first time investor and you are wondering when to start using a property manager.The property manager is probably the most important person on you team.

It would be our second up down house hack, however, with interest rates in the high 6's, it would probably not cash flow after moving out.

My team rehabs and builds new.  

But it turned out, it was his roommate (who moved in without telling me, but turned out to be a good tenant) that was doing the cleaning up.