Even with jailbreak, I generally found Winterboard annoying, so about the worst I ever did was install the 5-icon extension for the fixed bar and the status bar notification icons.
As for applications, I use the first two pages for frequently used apps. Third page is for games (of which I don't have many, but I like to be able to get to them reasonably often). Subsequent pages are for less frequently used (but not undesireable) apps. Finally, I reserve the rightmost page for built-in apps I would really rather uninstall... things I never use, or would prefer to have my eyes gouged out instead of using them.
The first page is populated (left/right/top/bottom) by:
- Messages
- Calendar
- Contacts
- Notes
- Snapture (app store version)
- Camera (mostly for video)
- Photos
- Mobile Fotos
- Tweetie
- Facebook
- iPod
- Shazam
- Maps
- Kindle
- Stanza
The fixed panel in the springboard is populated by:
- Phone
- Mail
- Safari
- BeejiveIM