It is an str already so the points about excess wear and tear are irrelevant.

Apparently, the Chicago Housing authority provides a one time incentive equal to the first month rent to first time owners participating in the program.

Having said that, the original author of the post do contribute a lot to answers on BP and I wouldn't take that away from him. 

I just checked out his web site and teasers.

I have a nice hi-rise condo unit and I get tons of companies asking if I do MTRs for Visiting Nurses, Tech Professionals, etc.My place is positioned near a number of large DC Metro Hospitals, but since covid work-from-home and recent lift of Eviction Moritorium, I have had few people with jobs, but a ton of people recently evicted looking to rent my place.The one viable group - visiting nurses has been excluded because my HOA will not allow short or mid-term rentals (anything less than one year is a No-No).They claim too many transient tenants cause excessive wear and tear on the property and too many people using resources like the gym, or pool or common areas.I think that's a lot of horse waste!

You should only consider switching when your current software has a significant flaw or lacks features that force you to spend excessive time on workarounds.

It 100% is possible to limits but you need to plan around the Excess Biz Loss rules from TCJA.

Is being a section 8 landlord there doable, or is the housing authority and the city a hinderance to deal with?

You should only consider switching when your current software has a significant flaw or lacks features that force you to spend excessive time on workarounds.

Then, roll the excess into rentals.I like your plan for keeping your exit strategy flexible for each acquisition.