I like the track day idea. Next time I'm in Birmingham I'll see if I can set one up (and that is such a nice track, but I've only seen it from the window of the museum).
Practicing in the rain is what I try to do, obviously but it is such an effort to force myself to go out there given my insecurity.
Another thing that caught me off guard was the difference between my Vstar-1100, all the Harleys I've ever riden, even the V-Max and this Victory. The Victory seems to behave very differently.
The first time I rode in the rain was when I drove the VStar to work the first week I had it (it was also my first motorcycle). It was a deluge type rain after work and the puddles were up to the middle of my front tire. There were trucks passing me spraying water in my face (I felt like I was inside a wave at the beach on occasion). There were time I couldn't see. I just had to chant to myself: "trust your gear, trust your gear". Braking wasn't the problem then.
I will look into a track day. As for dropping by on a rainy day... I live about 5 hours from Barbers... that would be difficult.
Thanks for all the input. I've been paying diligent attention to all the advice.