Progressive is very reasonable - even beat out the quote from good friend who owns a State Farm agency. I pay $137 a year for a 2002 KDX 220, and $62 a year for a 2002 6x12 enclosed trailer. Both have fire and theft coverage, trailer also has collision. Pretty cheap considering combined values are about $7,500.
Were you home when the bike was stolen? Looks like you live in a pretty rural area. Any dogs? Pretty ballsy guy if it was at night and you guys were home. Seems like it would make some noise breaking into a barn and loading up a bike. Either way you haul it, a bike in a pickup or trailer is not going to go unnoticed in a small town. Definitaly seems like this guy knew of you and the fact that you had a bike in the barn. I bet he's caught soon.
I hear stories like this all the time, so I am a little paranoid/anal about securing my stuff. Trailer is in the garage, and I still have a coupler and latch lock on all the time. Considering a wheel lock at this point!
Good luck!