Lightfall,
I just went through this same thing myself. I too have a chunk of money and a lot of hours into my bike. I wanted it to be insured for about what $ I have invested, not what an adjuster can find immediately available in the want ads if something were to happen to it. I am no expert on insurance, but this is how it went for me...
I looked into H_____ty Insurance, they advertise toward vintage restorations, custom builds and for 'occasional use vehicles'. I did not type out their name because they wasted my time.
Their application process was a bit over the top. If your 95 year-old granny lives with you will have to provide them with her drivers license number (along with all the other drivers in the household). It doesn't matter if granny does not have a class M license. After you finish all of your submittals and send in photos and proof that you own and insure other vehicles they call you.
My phone call felt a bit like a criminal interrogation and it did not go well. In the end, they were fine with the insured value I wanted but they did not like the fact that I would be riding the bike for pleasure. It was okay to ride it to a club event or a collector show but not okay to just go for a ride. The interviewer was not happy when I said I may put 2,000 miles on the bike in a season. They said that I should re-apply if I were to purchase another motorcycle to be a daily rider. I had told them I would be riding 2,000 miles a year when I filled out the application at the beginning. ...Waste of time.
Then I looked into Progressive Insurance. They had a straightforward online application process and an 'Agreed Value" category for which my motorcycle qualified. For values below $15,000 you are instructed to put together a file with all of your major receipts and four photographs of your bike. Save the file. If at sometime you file a claim you will need the file. An appraisal does become necessary if the agreed value you want hits $15,000. I did not need an appraisal. The insurance became active immediately upon clicking my mouse, (as easy as ordering parts).
All in all I think I have a good insurance package. Anybody out there ever file a claim on 'Agreed Value' with Progressive? ...........
XStretchified