It may be $20,000 this time around, even, given that this next update is both the biggest ever
I wasn't around back in the day but surely bringing in z levels was the biggest update?
Anyway, as for the actual thread;
Sure the UI is a problem (for some people anyway) but I don't think running a kickstarter and paying toady to do it is really a viable solution, first off i'm 99% sure he wouldn't agree to that, (he talked about his feelings about kickstarters and taking money from people for a specific bit of work in general on a df talk, couldn't tell you which) secondly, what if it takes more than a year, or the quality after a year isnt acceptable, and toady doesn't want to continue with ui stuff? (basing that off the fact he isn't doing it of his own accord, so he probably doesn't want to.)
Also, sure, having the ui for 20 years makes all of those 20 years more enjoyable, but doesn't any content? When the pending update comes won't the next 20 years all be better because of its features too?
UI improvements are no different to any other feature really; some people think it should be #1 priority, others don't, everything toady works on will improve the game experience (unless something goes wrong) and I don't believe the majority of players think that UI improvements are the most pressing or most important thing to add to the game. Don't ignore the priorities of the obsessive masochistic unemployed DF players.