In many cases this has been deferred and not uncommon to see 20-30K in immediate tree removal due to regular maintenance not being done on your typical 2-3 year intervals.Managers usually do a terrible job mowing as a complete service.  

But not in regular transactions.

Also, with spring coming, I may lose out on a longer term tenant.Opinions on whether I should take these tenants( assuming regular qualifications are met)? 

They deteriorate at a pretty accelerated rate compared to a regular home.

Here's my current situation-I have a full time job (30k income)that I am ready to go part time, I also own a part time cleaning business that I want to make full time (first year in business, so no tax returns yet) (brought in 30k last year but didn't show much profit).

Hopefully your post will generate some good input from Chicago folks who regularly advertise and who know the latest websites that get results.Apartments.com might be a good one.

You'd have to venture out in the secondary markets to find a clean deal above the 1% rule.You may want to investigate @Ben Robertsadvice and check out Memphis.

If not, just learning from someone who has been doing this regularly  would more than enough for my first couple of projects.  

So might as well go directly to the guys who do this on a regular basis.

Is their credit report good/clean?