Pro: In a conventional banking system, you have to trust people to handle your money properly along the way.

While you shouldn’t categorize all tenants and it’s the landlords responsibility to properly screen, the tenants who reside in better situated housing and pay higher rents are more financially responsible meaning lower rate of rent loss and will generally take better care of the property which combined will result in less time allocated towards management functions if self-performed or more favorable management fee structures if 3rd party management companies are utilized (which ties back to #1, as well).

Connect with local investors and experts for a house-hacking strategy and ensure proper permits for rental properties.Good luck!

Thanks James for the proper terminology.

@Anish KoshyThere is a lot of information out there on how to do your proper due diligence on a syndication, including the sponsor.

Make sure you are properly screening your leads the same as you would for long term renters. 

There are three items required to make a successful partnership - Time, Experience, Capital.If you are a syndicator, you are likely expected to have time and experience.There is a lot that goes into being a competent syndicator - Proper communications, finding a good deal, communicating quarterly updates, networking with lenders, contractors, PM companies.You can gain experience by doing your own deals or working for someone who does(Ideally both).I personally think you should cement your experience before worrying about OPM.Best of luck

Some buyers don't want your tenants who may or may not have been screen properly but some buyers like the attraction of having income on day one. 

If they deem your roof needs work when they evaluate it, you will have to re-roof first.If I had it to do over again with all the proper facts in front of me, I would probably have made a different decision.

Additionally the suburbs have higher taxes compared to Chicago proper.