Now that we've closed I'm adjusting to having 3 mortgages and managing the operations/expenses... baby steps. 

Bruh, if youre trying to compare multifamily homes in Chicago, which are 100-300 year old homes to new construction....then you really do have to re-adjust your expectations.

I would call up 3-5 property management companies and see what they would set rent at and why.

I'd recommend you follow your favorite forum topics and set up keyword alerts!

Or any tax strategies that I’m potentially missing out on by not setting it up in an LLC versus personal conventional mortgages?

Most investors are doing LLCs from my experience... but that doesnt mean you have to. there are some liability protections with LLC, along with a little anonymity if set up right. but also some added costs. one suggestion here is just whatever you decide, stick to it. some counties will see a transfer between personal/ LLC or vice a versa as a 'sale' and trigger property tax reassessment.  

Is it a unique setting? 

adjust your cashflow expectations?

@Luke Masaschi it sounds like you've already got it set up! 

I'm just lacking the knowledge as far as starting the business off correctly as far as LLC's and being legally set up beforehand.