If you’re leaning toward an LLC, I can recommend some local options to help set it up.

Highly recommend @Lien Vuong she commented below and has helped a lot of our clients start of expand their investment property portfolio. 

I would recommend tuning into Straight Up Chicago Investor Podcast and going to local meetups. 

Any recommendations? 

For those of you who are seasoned investors, I would greatly appreciate any recommendations you may have.

We recommend you get management contracts from several PMCs and compare the services they cover and, more importantly, what they each DO NOT cover.

Does anyone have a good inspector recommendation in Chicago northwest suburb ?

@Zach Howard some copy & paste advice below:)-------------------------------------------------------------------------------------------------Recommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

I would recommend considering conventional financing until you reach Fannie Mae's limit of 10 properties, then consider either a portfolio loan, and start your race to 10 again, or look at DSCR at that time. 

Third, I'll check in my resources to see if I can recommend an agent.