I've been researching STR regulations is various markets and many areas require a "local agent" that lives within 10-45 miles of the village.

Near the ski village?

The homes were built in the Auto industry boom.

@Ryan Dougherty I love the areas with strong economic drivers such as up and coming arts communities such as Charles VIllage/Remington and/or areas in proximity to hospitals such as the Hopkins so hence our decision to invest in the Patterson Park area.

I also have all of my other recurring expenses on auto pay.

That the operator name you as an additional insured and that their Insurance company agrees to give you 30 day notice of cancelation or non-renewal2. the Operators Insurance company agrees that their policy is "Primary & Non-Contributory" and that they waive Subrogation against you.The Agent can also help with what you should be requiring of the operator for Limits of Liability and coverage (Liability, Professional Liability, Workers Comp, employment practices, Cyber Liability, Auto, etc...)Bring those suggestions to the Attorney drafting your Lease agreement with the operator and have them incorporate them or versions the attorney suggests into the contract. 

Hungarian Village might be considered 'C', but is negligible in distance to downtown/German Village from 'B' Merion Village or Southern Orchards; it's also one of the next areas to rise considerably in value.Yes, there are clear areas with lowest incomes, values, most crime, poorest transit, etc. - beyond that, there is a lot of opportunity even in areas that many would write off.

Wondering what property management companies you would recommend for Chicago Ukrainian Village/Lincoln park small properties?  

You might be able to afford more than you think.Check out as well Little Village - I was featured in a Univision report the other week (see my FB page) about the area gentrifying.

I currently have a real estate agent I am working with (just the same agent I bought my primary residence with), and he seems to do everything I really think an agent is useful for, i.e. showing me properties, quick responses, MLS auto-updates, etc.Recently, I called a local PM company in the VA Beach area (found him at random, just chose the one with the highest ratings from Google search) to check up on average rent amounts in a particular neighborhood.