I somehow have the impression that in the early days of Twitter, noone cared. Later, the people behind the hashtag idea seem to have underestimated the user requirements complexity.
But what would a solution for the current “experience” boil-down to? Either a better syntax for “extended” hashtags or a better “server-sided parsing” of the text sent. Having the latter would again mean to hide the control about what is possible from the user… much like it is now. If I was to take the decision, I would opt for the first way:
Besides the #tag (would be supported for, errr… compatibility), there could be the “extended” syntax that goes #[tag] with everything in between the square brackets being the text to “hash”. Yes I know -sigh- it will waste another 2 characters from the precious 140 budget, but think of the benefits.
( BTW, there’s always a way to save 2 chars from a tweet, right? If you can’t find your tweet fitting into less than exactly 140 characters, you probably should think about rephrasing it anyway…)
The funny (or sad) thing about the above idea is, that it didn’t take months of investigation and reading technical specs to come up with it: It’s simply borrowed from Wikis… something that was around before there was Twitter IIRC.