tinyE: I've started playing all my Steam games in Off-Line mode.
This seems too good to be true. Am I setting myself up for something awful?
Generally speaking you'll just miss achievements and cards, if you care about those (you probably don't, I'm just saying). Other than that, there are games that might cut some features when you're not online (e.g. X3 Terran Conflict) or fail to validate DLC, but that's more game-dependant than steam-dependant.
kbnrylaec: I do not know if it is true, but some info said that Steam off-line mode is not permanent.
You have to login monthly or so.
It's supposed to last indefinitely, but it never worked that well for me. Back in 2011 it was a huge pain in the ass, had to relog at least once a week or so, but they improved it a lot over time. Now I can stay offline for months without issues.