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To install a game through Steam you need to be online. This is true even if you have all the files already on your drive - it'll insist on checking the servers to confirm they're the right copies, and the Steam launcher won't let you start a game until its checked it for updates at least once (and installed anything it happens to find).
Once a game has been launched at least once, you're generally good to go in offline mode. If you go online and more updates are found, though, Steam'll block that game from play again (online or offline) until they're installed. Games which lack DRM can still be started from outside of the Steam launcher, though.
Offline mode doesn't have an official "time limit" on it, as such. It just tends to bug out at random intervals, forcing players to go online again before they can re-activate it. Users who are affected are often able to get it working again by changing their system clock, but how long the mode works for after you enter it seems random... days, weeks, months, reports are highly variable. Valve says it's not supposed to stop at all.