If your tenants want 68 degree units they can pay an extra $50 or so apiece per month for each window unit.

I’d rather have the hard truth than a sweet lie.

Quote from @Devin Dorame: @David Colthart Before you invest or buy in The City of Cleveland I would suggest you google "Tenants First Initiative" and become aware of all the extra fees and problems the City of Cleveland gives "Out Of State Investors".

Every contractor knows this is the gospel truth.

Well that's what I'm trying to figure out, from a room-mate perspective, if the decrease in what the two non en-suite bedrooms needing to share a bathroom with a third (fourth in total) roommate is worth the extra rent I could charge. 

If your tenant demands they work outside of those hours, then they have to pay the extra cost the contractor may charge for after-hours work (typically 50% more).I recommend you take control of the situation.

It is annoying but if the extra occupancy calls for it it is worth the hassle.

I not only paid him his finders fee but gave hime $5k extra because he had to do more work to make the sale happen than he intended and because it was a good purchase for us.  

As far as renting garages or extra space my insurance will not allow me to rent anything to a non-resident.

I know here there are several extra requirements for a property to be used as an assisted living facility.