@Ananth Subramanian follow your lease terms and landlord/tenant laws.

Our law firm is seeing an increase in eviction filings this year.

More often, I see people in Chicago using the MTR strategy to side step the STR regulations.I've considered buying a SFH with an in-law arrangement in Chicago to use as an STR because to me that seems like the best way to employ the strategy.

This way, if you have a legal fight, you're fully covered by that state's law.

My first recommendation is to check your state laws regarding wholesaling.

Typically you do not need to give 60 day notice, more like 3 days....law says one thing, but judges may not always follow the law, so I say send it to the tenant, send another certified with return receipt, AND post it on the back the of the front door or give it to them in person.   

Just be sure to optimize for location within that market as much as your budget will allow and also make sure you are compliant with local laws. 

It is basically everything I do in my local market....I'd love to go with a local property manager but they hide behind fair housing laws and say the property owner cannot refuse whatever tenant they pick.

The other half are caveat emptor.2) When buying through an individual that likely isn't following state real estate laws already since they likely are in violation of the state brokers act....you probably arnt getting a disclosure even if state law requires it.

Each state has their own eviction laws, and I would want you to set up it right on the front end.From what you've written, whoever has the ownership shoudl be the landlord on the lease.