Thanks for the words of encouragement; I'm not in the Chicago area; the property is in Bureau County. 

So if a landlord who is taking all the risk wants to eliminate some of the risk by not renting to people who have already shown that they cannot play by societies rules, so be it.

But thank you for your help, and encouraging words.  

@Krishna SurendraRecommend exploring as many sources as possible to get referrals AND cross-reference them to get as much accurate information as possible.Check out NARPM.com, BP’s Property Manager Finder (BiggerPockets: The Real Estate Investing Social Network), etc.Also, encourage you to learn from the mistakes of others - by reading posts here on BiggerPockets about owners not having their expectations met by their current Property Management Company.

They are a much forgotten group and that's kind of a disgrace.I also have great deals cross my desk all the time in PA and S.Jersey, be happy to share if you ever wanted to take a look.Thank you for the encouragement.

But I try to encourage my clients to value time to market. 

I would also encourage you to keep building up cash reserves, you're going to need them. 

Encouraging your tenant to consider vaping could not only help maintain the apartment’s air quality but also align with your lease agreement better.

Give him the option of staying in place with a major increase, but keep rent about 10% below market to encourage him to stay.

Any tax advisor you happen to find that encourages sketchy positions or fraud on the position that "they probably won't find it" - run for the hills.