Would I do it again - yes, in fact I am doing it agin with TH. Would it have been easier with hindsight of every twist and turn in its development - sure. But I didn't have that luxury with any of my other pins so guess it is not fair to have expected it for WOZ.
It is easy to second guess your actions and rationalize, "if I had waited for this or that to happen, I could have maximized my purchase or minimized my downtime". But It was an opportunity to get in on the ground floor of a new company making a classic family-themed pin, and the experience was fantastic!