Pierre32 wrote on 2022-07-19, 21:46:
LAN is the best method. You'll never go back.
Ideally, if you have some spare hardware (old PC or Pi) set it up as a server running RetroNAS. That means you don't have to think about how to get old & new systems talking to each other, juggling different SMB versions etc - it makes it all pretty seamless.
Seconded. LAN makes things a lot easier. You may even be able to skip the whole "transfer" bit entirely and just access files and run programs straight from network drives. My approach is if it can be networked, it will be networked and it will have network drives - I can't be bothered copying stuff around with FTP. DOS 3.0+, OS/2 1.1+, Classic Mac, all versions of Windows, all unix-like will all do network drives fine. The only limitation is if the machine has no expansion slots at all and no built-in networking - so basically very old laptops and weird things.
Security isn't a big concern - I'm not forwarding ports on my router to Windows 95 and I'm not using a web browser on Windows 95 so for someone on the internet to talk to my windows 95 box they'd have to already be inside my lan in which case I've got bigger problems than my Windows 95 box being hacked. But its possible to do network drives without using TCP/IP at all making the computer completely invisible to modern windows and the internet in general which only understand IP.
Removable media (CF Cards, DVDs, CDs, flash drives, floppy disks, physically moving hard disks around) are a method of second-to-last resort. I'd use them only if network wasn't an option. Inconvenient and slow but its hard (not impossbile) to install an OS and get a computer on the network without at least one floppy disk or CD.
If it can't be networked and removable media isn't workable there is always a serial cable or parallel cable. Laplink, fastlynx, Kermit (which is available for windows and just about everything else), and probably lots of others.