Looking at 4-5 months from initial offer to listing and I have a GC handling all the work, so my time has been just driving to check status/give input/drop off payment.

@Michael Plaks is spot on - character wise, 1099-R income falls in the same "bucket" as a W-2 wage would be, thus to offset this income with real estate losses, it follows the exact same pathway (ST rental with material participation or REP status with traditional rentals), but since you don't have all your time sucked up with a W-2 job, you have much greater flexibility to hit those related hours thresholds under those paths as well.No idea if he's taking clients - but if you are looking for local(ish) and qualified in TX, Michael is also likely a great one to reach out to.

My thoughts are trying self management at that time (with many disclaimers on my Airbnb listing that the main pool is off limits to my guests).If it goes well I will keep it.

My guests (they are not tenants) have to get into the rentals at all hours of the day, so no one meets them to give them a key and let them in.  

Maybe limit the guest size in the house to 3 or 4 so it can't get too crazy. 

Hopefully, the guests are able to unlock & lock the door despite the cold.

The specific location ( 4' * 6' long) is underneath a guest bedroom window in the front of the house. 

I worked for IHG, the hotel chain, and if you are a franchisee, the home company can easily remove your status as a franchisee. 

I did get my first guest, on AirBnb, who booked for 70 nights.

It sounds like you might already be aware of this, but the only time you can put a rental property on a Schedule C is if you provide those "hotel-like hospitality services" that you mentioned, which means things like not just cleaning between guests, but daily cleanings during guest stays, and/or providing them with things like meals or entertainment during their stay.