Our latest gear purchase was a Garmin Forerunner 305. I can't believe how handy it has turned out to be, and I have yet to read the manual which I suspect will make it even more useful. We just got two bike mounts delivered yesterday but I had used it on two rides already. Once by wearing it on my wrist the second time I just put it in a jersey pocket. I tend to look at it too often if I'm wearing the heart rate strap, maybe that will pass as the newness wears off.
I have been using Buckeye Outdoors to log both my running and cycling and the Garmin data can be synced to Buckeye Outdoors by using Sport Tracks a free program that will keep data locally on your computer as well as handle the upload to an Buckeye Outdoors account. One fault I have found is that the route maps are uploaded allowing public access so you need to make each one private if you don't want people knowing where you live. I'll be looking at this more and post an update if I find an easier way to keep things private.
Buckeye Outdoors has a sister site Go Wagon which I was using before trying Buckeye which I find I like better. If you sign up for one you can use the same name and password to sign-in to the other as well. A Go Wagon account comes in handy if you want to use Twitter, Go Wagon will update your Twitter account with your posted workout data. So what I've ended up with is a long string of programs that all work to put out info on twitter that no one likely cares about. The nice thing is so far they all work without fail and it is all free.
If anyone wants to follow Jenny or I on Twitter we can be found at @doitalloutside, and @redbaja respectively.