Quote from @Garrett Brown: Hey Kyle, you are taking the proper steps by switching in the long run.

These are the options I'm currently exploring:Do the proper notice on the 3 month to month units and stagger the increases, starting asap, so I only risk losing one tenant at a time.

If the unit does not comply with local codes (like proper egress, zoning approvals, safety standards, etc), it cannot be legally rented regardless of how it’s marketed.The safest course of action forward, would be to bring the unit up to compliance with chicago's zoning/ building codes before attempting to rent or advertise it. 

     Firstly, this post is for anyone and everyone who hasn't had the opportunity to properly introduce themselves in the BP community.

@Minnina SmithTo buy your first rental property, assess your financial situation, educate yourself on real estate investing, set goals, build a team, analyze deals, get pre-approved for loans, and start property hunting.

Fix it properly, then rent it out to a highly qualified applicant. 

Maintain proper records, such as contracts, settlement statements, and promissory notes.4.

Other ideas that have captured my attention are finding a 4 bed/1.5 bath house that has room to add a stand up shower to make it a proper 4/2. 

Make sure your LLC is set up properly, and consider hard money lenders for more flexible options.

As someone who lives in Dallas proper, and gets good natured annoyed when some one who lives in Plano says they live in "Dallas" they places you mentioned would make folks who live in Prosper blush (40 miles from Dallas) blush.