I can completely relate to that.
The strange thing about bitcoin (to me at least) is the "purity" of the speculation. Since it has no connection with anything tangible, and is not backed or supported by any organization with an interest in moderating price, it seems that there is no basis for price other than psychological ones. Is there any other market that can boast the same? There are not even any circuit breakers or trade limits that I know of.
Oh sure, yes. There are futures markets that get badly misaligned with the underlying -- but the underlying still has a substantial moderating influence.
At the same time, bitcoin also seems particularly susceptible to manipulation, and more than a bit opaque (at least to me).
Perhaps I am mostly just crying "sour grapes". Wish I'd bought so many times. We started to really talk about it in the office here at about $1200. Almost every day it went up and up, and almost every day I said "its at the top now".
Incidentally, an outsider who checked into my personal trading would conclude that my general trading strategy has been "buy high sell low".