@Keri Win how much time do you think you'll have to invest to learn how to properly manage your rental?

:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

As long as you're making payments on time and have proper insurance on the property, banks are happy and don't want to call a loan due. 

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).

Or are these two completely separate things that do not coordinate together?   

It has to be handled in the proper way.

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.  

.), 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)?