All my retro stuff is backed up to a 1TB SSD and only used when I need to put something on my retro-boxes via network or FTP. While there's more on there than just retro stuff, I have this folder structure
RETRO
- DOSGAMES - I have them by alphabet (mostly) with special subfolders for Ultima, Maxis, SCUMM, and Sierra stuff since most of my favorites are in those folders. Bigger stuff like the 7th Guest, Killing Moon, Lighthouse....etc....are stored as ISO & VCD files so I can run them without the CD on the go
- Win16 Games - I just have the installers doubled up in the working program folder so I can install if it has an installer, or just copy the folder and make a shortcut if it does'nt. Some games that require the CD have an ISO File and VCD File depending on if I'm using shsucdx in Win31 or Virtual CD ROM in Win9x.
- Win32 Games - Usually 2 CD images, ISO or VCD again, like before, and then the regular installer in a base directlry in case it does not require the CD on an actual CD-ROM drive.
- Emulators - This is all the old emulators for DOS/Win9x that I use, NESticle, GeneCyst, A26, Z26, MAME, and all that mess + ROM Hacking utilities for NES in the ROMHACK directory
When installed on the computer I structure my HDD this way...
C:\ - O/S, major program files, internet applications, data xfer tools, etc...drivers...
D:\ - Utilities, Programs, Programming Development, Graphics, etc...
E:\ - An entire partition just for games and emulators
F:\ - Media - NSF Files, MP3s, MIDIs, OS ISO/VCD files, DRiver Disks/installers, PRogram Installers, and of course, the CD image Files for the games are stored here when using SHSUCDX or VCD
Usually when I do file copy over network, I just start a heaping mess - were talking GIGABYTES of data here - and let it run over night. FTP though I have to monitor because for some crazy reason FileZilla tries to copy over multiple files at once and causes some copies to fail. Most of the time though I just slap the HDD (if it can read it) into a modern PC and copy that way. I use huge HDD and sometimes I can make all partitions readable, especially if I use MaxBlast as my DDO and do all the partitioning within MaxBlast.