Take ownership of your mistake and learn to do the proper due diligence recommended above😊 

While you shouldn’t categorize all tenants and it’s the landlords responsibility to properly screen, the tenants who reside in better situated housing and pay higher rents are more financially responsible meaning lower rate of rent loss and will generally take better care of the property which combined will result in less time allocated towards management functions if self-performed or more favorable management fee structures if 3rd party management companies are utilized (which ties back to #1, as well).

Some buyers don't want your tenants who may or may not have been screen properly but some buyers like the attraction of having income on day one. 

Additionally the suburbs have higher taxes compared to Chicago proper.  

It has to be handled in the proper way.

.), please describe for me the worst-case scenario for an eviction process if the tenant refuses to leave at the end of a lease term (assuming I do everything properly according to MA laws)?

If I were to apply for a CFO role now, more than likely I have to advantage over a CFO that was in a manufacturing company for a real estate company.EAs specializes specifically in taxationCPAs have a broader knowledge for accounting, auditing, financial planning, and taxation.EA must pass a 3-part IRS exam and do not require a college degreeCPA need a degree in accounting, 150 credit hours of education, must a 4-part CPA exam.EAs often charge a lower fees

A little further from home you'll find some of the value you are looking for in Kentucky, another state that is supportive of manufacturing and in following the state Economic Development you'll see chomping at the bit for more manufacturing. 

It sounds like you are already doing move-ins perfectly with photo evidence and proper documentation.

.- Inform your tenants about the proper use of the dumpster.Each tenant should be responsible for taking out their own trash on the designated collection days, but having a common dumpster is usually more convenient and cost-effective.Remember, clear communication with your tenants is key.