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I'm going to post some info about Offline Mode based on my experience and research. I have about 423 games on Steam so I played with the client many times.
•Steam's Offline Mode for the most of the time requires you to use the "Go Offline" feature from the "Steam" menu at least once when you have the Internet connection. This ensures Steam to create an auth cache so it doesn't need to validate you while on offline. This practice is a bit weird and that is why people really don't do this and complain that Offline Mode doesn't work. It is a valid complaint.
•Sometimes, the auth cache is created without having to use "Go Offline". I have yet to figure out when or how exactly it is created, but it has to do with Steam server going maintenance while you are connected, your Internet connection briefly being dropped or such and getting back online. Steam never creates the cache while you are online for all I know. This is the reason why sometimes people say that they never had a problem using Offline Mode without having to use the "Go Offline" feature.
•Even with the cache is created there are rare occasions where it would still not allow you to go on Offline mode. This is due to quitting Steam while it's still refreshing the whole cache for content updates and downloads.
•When the Internet connection is dropped or selective networks are blocked in your connection while the computer is connected to a host (or in a network), Steam will try its best to use the network to connect to the Steam network servers. This most of the time allows users to use Offline Mode, but it takes time to get that prompt. This is why on some restrictive networks like university or workplace Internets Steam takes longer to launch. If you don't like it and you don't need that connection simply disconnect from the network.
•There is a way to play Offline Mode without having the auth cache. It's to force Steam to boot on Offline Mode. You can easily do this by going into the Steam installation folder (where your Steam client, "steam.exe" is located), and creating a file named, "steam.cfg" with contents of:
BootStrapperInhibitAll=enable ForceOfflineMode=enable
Note that by default Windows computer hides extensions of files so if this method does not work it is likely that the file is named as, "steam.cfg.txt". You can easily fix this by going into any explorer window (a folder or such), Tools (by pressing Alt if you can't see it at the top) -> Folder options -> View tab and unchecking the item, "hide extensions for known file types". This will reveal the extensions of your files. If you don't like it, you can change it back any time after you confirm the extension of that configuration file for Steam.
So in the end, everyone is correct. They have reasons to complain about the feature and a lot of the complaints are valid.
EDIT: I FORGOT TO ADD THIS!!
•Some of the Steam games REQUIRE you to launch it at least once when you have the connection to the Internet. This is NOT a part of Steam feature, but the developer's own in the game. I'm pretty sure you can find the list with a little bit of a research. I know at least one that requires this. It's the "Titan Quest" series.