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https://gaming.stackexchange.com/questions/346858/how-to-keep-steam-in-offline-mode
I mean on some level online digital distribution systems that also function as DRM aren't the best choice for someone who doesn't have internet. He's just not the target demographic for online services.
Generally speaking he should have been fine for longer than two days, so I'm wondering what he did to trigger the need to login. Restarted the PC, or shut Steam completely down maybe? It's hard to say because being a middleman for someone who doesn't know what they're doing is really difficult.
Steam's offline mode is meant to be indefinite. Games themselves may have to sync to various DRM servers every now and again, but offline mode is just meant to keep working until you switch it off.
https://www.pcgamesn.com/steam-offline-mode-designed-be-indefinite-valve-are-working-make-it-more-robust
If its games you should be able to play without if its Steam also. Just add a straight through cable from his to yours and he can update via your internet.
Or add a wireless network adapter and use for updating. Then unplug.
Steam itself has a good selection of games that you can start without the client. GOG, with its catalog (mostly) focused on DRM-free titles is the best friend of the offline gamer as well and the Epic Game Store, with half its catalog DRM-free is also a suitable mainstream option.
https://www.pcgamingwiki.com/wiki/List_of_DRM-free_games
Good luck
A few years ago I didn't have an internet connection for 5 months. I had no problem opening Steam in offline mode for the entire 5 months, and I was able to play all the games that I had planned to play.
Every game that he wants to play offline will need to be started once while he has an internet connection for the first-time setup before he can play them in offline mode.
Is he using some program to "clean" his computer? That might be removing Steam's cookies.
Did he check the setting in the login screen to save his login information? Offline mode requires login information saved while he is online.
And he should click on Steam in the top left corner, select Settings from the drop down menu, and make sure that he did NOT put a check in this box:
After he is done setting that all up again when he has an internet connection, tell him to make sure he disables the wifi network connection again.