I've been riding a lot of hills recently, getting ready for the 7 Hills of Kirkland on Memorial Day, and I'm getting more used to climbing and less scared of the steeper hills.
But I've found that there is a dearth of information about the various hills that I ride on. The best source that I've found is the "Larry Kemp climb spreadsheet", which has some good information, but doesn't cover a lot of hills (Larry was killed while bicycling in Europe last spring, and there haven't been any updates since then).
Every few months, some of the less-experienced riders will ask about routes to get from A to B, and it's really hard to quantify how hard a specific hill is. How does Inglewood compare to Factoria? What about Lake Hills Connector? (for those of you who haven't yet picked up on the exciting hobby of learning hill names in the eastern suburbs of Seattle, bear with me...)
I'd looked at a couple of topo programs in the past, but the front runner - TopoUSA from DeLorme - was about $100, which was a bit too rich. When I checked last week, I found that I could get an edition for the western US for only $50, so I ordered up a copy, and installed it on my laptop.
This is a cool and powerful tool. You can set up routes and get their profiles, and supposedly, you can add your own trails (which should be nice because bike routes aren't in MapPoint...), and download the routes to your GPS (which I might use for RSVP this year). It does most of the calculations that you want.
But, the user interface looks like it was designed in 1987 to run on X Windows. It doesn't use any of the standard Windows UI approaches, so it's really hard to figure how to use it initially. No menu bar, for example.
Overall, I think that it's pretty good. The map database isn't as good as mappoint is - I know the roads that I ride pretty well, and the mappoint layout seems very good. The TopoUSA version has slight turns where the road is straight, and some turns are sharper than they really are. But, overally, for what I got it for, it's okay.
I haven't yet verified how good the elevation data is yet.