The Bold is a wonderful high end phone. It's one of AT&T's most expensive, so you might want to also consider the BlackBerry Curve 8320, which also does email, has a calendar and WiFi for HotSpots (your son won't thank me for telling you this though). The drawback with BlackBerry phones is that their OS is built around that cellular data connection you're trying to avoid, so some services won't work on the phone. But the WiFi web browser and voice will certainly work.
The other challenge with getting a smartphone is that the dealer will try very hard to sell you a data plan with the phone. so you'll have to insist you don't want one (the BlackBerry data plan costs as much as the iPhone plan but isn't mandatory). Most rebates on smartphones do require a data plan for the first 3 months of the contract, so don't count on getting one.
Other smartphones with WiFi, email, calendar and full keyboards include the Samsung BlackJack II and Samsung Epix. These run Windows Mobile and work fine without a data plan (be sure to have your son turn off cellular data on the phone to avoid accidental charges). Both phones are relatively reasonable, especially the BlackJack II.
For you the choice is wider since it sounds like you don't need WiFi (Hotspots), just the calendar. Most phones have a calendar these days, and if you choose on with a QWERTY keyboard, entering appointments is fairly painless.
-------------------- Lisa Gade Editor in Chief, MobileTechReview