8gig files on an amiga ? Using what file system ?
As for the general theme of the thread though, I must say that Ive never had any major dramas using larger drives. The only exception I guess being the boot partition size being restricted to 4gig, but that's no major hassle for such a small OS. I really dislike having many partitions (I use 6 on a 320 gig drive including the 4 gig OS partition) and it was as easy as pie to set up using os3.9 hdtoolbox. Once the partitions where defined I just installed pfs3 (I dont like sfs for reasons that aren't really important here) and changed and created the pfs partitions. Was as easy as setting up partitions on any other more mainstream OS.
It's pretty easy to fill the space though. Nightlong alone is a few gig of space, Descent:freespace 500+meg, quake 1, quake2, Napalm, Earth2140, lots and lots of whdload installed games, development software, emulator rom images and lots more. Sure, amiga software is typically a lot more basic than software for other systems, but there's so much stuff out there that it's easy enough to use as much storage space as you can throw at it.