I live 2 hours out of the city, so having my own property to book and stay in would provide a huge personal benefit in terms of being able to head into the city more without the stress or hotel fees.I guess I'm mostly hoping to hear if anyone has done this ... my initial concerns are (1) potential complexities with how the entity is set up/ business or otherwise/managing the books, (2) negative perception among vacationers in a complex or duplex format, and (3) finding a property manager that can manage some of the nuance of STR (such as cleanings) with the general maintenance of LTR.

Better to start sooner than later and clean house asap.

Ive been quoted a range from 22 - 29% for full service management (cleaning, consumables, marketing, collections, online inquiries, etc) - curious if others have any recommendations on  a solid company with a good rate.  

I will echo @Robert O'Keefe and say that management will give you a crash course to be able to transition into other things much easier than going in cold- but prepare to get some gray hairs and some 2AM phone calls.

I do have a couple of contacts in the city so even finding a new tenant and cleaning up one of the apartments does not really worry me too much. 

The city seems to be cleaning up its act and getting in now could mean staggering potential upside in the next few years. 

If you think the market likes the old style radiators, then you can clean them up, paint them and use them with a standard furnace with circulation pumps.

The carpet is so stain resistant that a Sharpie permanent marker cannot stain it; also bleach will not damage it.We also use stain guard pad with the carpet that will not allow liquids, and pet urine to penetrate into the pad or flooring below.When tenants moved out, we require them to have the carpets professionally cleaned.

Unless someone trashes a property $1,000 more than covers cleaning and some paint.

These alone prevent midnight "my toilet is plugged up calls" a.Landlord informs the Tenant that the sewer system of the Premises is not designed to accept many types of items, included but not limited to, paper diapers, sanitary napkins, tampons, and children’s toys, balls of hair, grease, oil, table scraps, clothing, rags, sand, dirt, rocks or newspaper.