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For the last two year's I've only raced one TT a year and its the Breckland trying to get 300.
It's clearly possible but it's a lot of pain and stress and work to go through to add a few hundred more yards. I'm not sure I've ever had a "best season" - the problem with focusing all your efforts on one race, one target, per year is that there's nothing else there when you fail.
Anyone wanna buy a Shiv?
Yes, of course they're arbitary numbers, but sometimes they happen to fall out on the right side.
I don't think you should sell up now. For what it's worth, I had my best ever TT season when I was 41/42, and I'd been trying for a long time before that!