Wow I just realized I almost forgot to update you guys on the insurance issue! I guess it ended up being such a non-issue in the end that I completely overlooked it.
If you remember, since I didn't buy Charlie for any set amount of money he was only insured for $3500 last year which was the base price Markel was willing to risk (here's the original post). Then I got a letter last month stating they were no longer offering medical/surgical coverage for horses valued under $5000 (basically I'd only get his mortality value of $3500, which I don't really care about; it's the surgical coverage I wanted in the first place). So I was really worried about how I could prove his value at $5000 without having done any shows or spent money/time with a trainer (since I'm doing all of his training).
Turns out I was worried for nothing. After speaking with Markel, I found out that in the absence of the above two validation options (shows and trainer) I could write a document stating Charlie's progress since last year and why I feel his value is worth increasing. So I wrote about how I am doing his training, spending 4-5 days a week on him, and about how he was almost unrideable when I first got him. I detailed his accomplishments on the ground and under saddle up to this point, which aren't monumental to some but still it's an improvement. Plus I looked up comparable horses for sale in the area and included their value (generally $4000-7000).....and they accepted!
So Charlie is (thankfully) still insured, now with $5000 mortality, $2500 colic-specific coverage, and an additional $5000 medical/surgical coverage for anything else, and I didn't even have to change companies :)
Insurance is totally worth it in my opinion. While I know I may never need it, in the past two months two separate horses at my barn have independently racked up vet bills in the $3000-6000 range from random accidents and that is way too much for my bank account to handle if something like that would happen to Charlie. I'll gladly pay my $495/year knowing that I'll only have to pay a $400 deductible. Markel can take care of the rest!