Firstly, "
Bitcoin Technical Support" is probably the better board to move this thread to. It is for "Questions regarding issues with Bitcoin Core, nodes, the Bitcoin network, transactions, and addresses"
As for your other questions:
Questions:
1. If I keep the wallets offline, can I just drag them onto a USB stick, and then, when I need them, drag them back to their initial folder?
Are you proposing deleting the wallet file(s) from your PC after you have finished using it each time and just maintaining the backups on the USB?
If so, every time you wanted to "use" your wallet (to get a receive address or send some bitcoins) you would need to do the following:
Step 1. Shut down Bitcoin Core
Step 2. Copy wallet file(s) from USB to Bitcoin Core "data directory"
Step 3. Restart Bitcoin Core (using the
-wallet commandline argument to specify the wallet file(s) you want to use)
Step 4. Conduct transactions etc
Step 5. Shutdown Bitcoin Core
Step 6. Copy the wallet file(s) from Bitcoin Core "data directory" back to USB
Step 7. Delete wallet file(s) from "data directory"
Step 8. Restart Bitcoin Core
You need to shut down Bitcoin Core before copying/deleting the wallet files to prevent wallet file corruption. Theoretically, you could use the "File -> Backup Wallets" command in Bitcoin Core to take care of Step 6
before you shut down Bitcoin Core, but you would still need to shutdown Bitcoin Core to be able to delete the wallet files from the PC anyway.
Is there any particular reason why you don't want the wallet files stored on the PC and want to move them back and forth from the USB?
It's a lot of hassle... and simply leaving the (encrypted) wallet files on the PC and having backup copies of the .dat files on the USB would be considered the "normal" workflow.
2. Do I need to back-up the two wallets into separate files? (Eg. wallet1.dat and wallet2.dat).
Yes
3. Or there a way to back up all of my Bitcoin Core wallets in one file?
No
4. Will a wallet backup file contain all relevant information about my private keys in that wallet?
Yes
Or do I need to also write out the private key information on paper?
No