I never had a problem getting insurance. Normally, after getting the registration taken care of I just called my insurer and told them what I have and how much insurance I wanted. The bill came in the mail.
Two weeks ago I bought a trailer out of state. I called my insurer the day before I actually picked up and owned the trailer, gave them the VIN # and told them I was purchasing tomorrow. So I was able to insure before I owned.
If you have a title, the vehicle has been registered, and has a license plate, I would think you could easily get insurance.
2014 Silverado 1500 Crew Cab 5.3L maximum trailering package (yes, I'm towing the 34')