S - the WannaBe text browser is good on the older Powerbooks, I use it frequently. You could set that site to be the home page for him. The URL window is funky, you have to highlight and replace the whole URL with WB, double or triple clicking does not select the whole current URL.

I use Eudora 6.2 to "fetch" things from my Hotmail account, it was tricky to get set up right but once you have that done, works well. When it pulls mail, though, it deletes them from my Hotmail inbox. I am sure there's a setting to stop that, I've just been too lazy to poke around. But I guess the native setting is "download and delete."

Good luck! The 5300 and 1400 are great form factors, if the 5300 is just too slow for him, try a 1400/166 with maximum RAM, it is still a useable web machine, using Classilla and WannaBe.