Someone I've been thinking about for a couple years - Climb Kilimanjaro before the glaciers melt !
From what I've heard it's not easy, but definitely easier than true mountain climbing: you basically walk up, and your porters carry a lot of the stuff. You hire then as a team (that being their normal work).
I've heard it takes about 5 days to climb up and about 1.5 - 2 to climb down. You cover less distance per day as you ascend. The last couple thousand feet are the hardest, due to lack of oxygen.
If you're in reasonably good shape you should be able to do it. But unless you know your reaction to low oxygen levels are (from previous high altitude work), there's the danger of health problems that may force you to descend before making it to the top. (I personally have no idea how I'll handle it. It would be good to find out beforehand though.)
The cost isn't bad if you're not on one of those outrageously-priced packages you see on the internet. I have a friend who did it for about $3000-$4000.
I'm thinking September this year (2008) - warm at the foothills, but not too bitter at the top.
Think about it, and the great photo ops!!!!!!
GB