My 386 / 386SX rigs -> MS-DOS 6.22 and Windows 3.11 only (not active computers, just for nostalgia purposes)
My Pentium MMX and PIII rigs -> MS-DOS 6.22/Windows 3.11, Windows 95, and Windows 98 multiboot. (both active)
And no, I don't have any problem with 2GB MS-DOS partitions. During the times, my last MS-DOS machine had a 500MB HDD, and I never even had a greater than 2GB HDD until Windows 98 was the system of choice.
Both of the active rigs has a decent sized (72GB for MMX and 146GB for PIII) SCSI disk in them just for storage purposes (ISOs and zips of uninstalled apps/games) so only thing I need to do is boot from W98 partition and just copy anything you need to the 2GB DOS partition.
For extra data transfer purposes, all my rigs has external CF-IDE adapters, and W98 capable rigs have USB CF readers. I tried CDROM (too wasteful), ZIP drive (too slow), network (too much hassle) and floppy (yeah, right..) approaches before, for data transfer, but nothing beats CF to IDE adapter, IMHO.
GA-6VTXE PIII 1.4+512MB
Geforce4 Ti 4200 64MB
Diamond Monster 3D 12MB SLI
SB AWE64 PNP+32MB
120GB IDE Samsung/80GB IDE Seagate/146GB SCSI Compaq/73GB SCSI IBM
Adaptec AHA29160
3com 3C905B-TX
Gotek+CF Reader
MSDOS 6.22+Win 3.11/95 OSR2.1/98SE/ME/2000