Have you just installed XP at home (in the last month or so), becuase if so, this explains the fact you can add stuff quickly. I think how it works is Windows keeps a count of the number of times you click a shortcut and adds the top 5 accordingly. I like your last program idea - shame MS never thought of that .
Unfortunately, I don't think there is a way to make stuff do this. My syggestion is to make the start menu bigger, so something like 8 or 10 programs display. You can also make the icons tiny, so you can fit loads in. If you do this, I'm sure you'll get the one you want. Just right-click on the start button and fiddle in the properlies. Good luck.

I stopped the whole thing by setting the number of adding programs to the startmenu-list to '0' and customized it myself. (Sorry, I don't know what this parameter ist called in the english version...) So all the programs I really need often are there. BTW, does somebody know how to get a user-pic in the startmenu when connected to a domain ???

I made several specialized toolbars. Then I dragged them to the side so they were hidden. I named them with a single letter to make their appearance smaller. So on the corner of my task bar is a tab for a,p,t,s with all the things I use most available instantly. I hardly ever had to open the start menu. Then I discovered object bar which does the same thing 100 times better! I really like object bars.