OK, My players, when they are creating their characters, always take some time to figure what skills they're gonna get.
But they usually don't care about gather info skill.
And actually, from all the skills, gather info is one(in my opinion) of several "weak" skills, let's say.
You don't actually need to have it, except if you are a bard or rogue or can 'waste' skill points, and even though you usually just get 3-5 ranks on it.
The reason I think this happen is that you can simply ask questions, don't having to make a gather info test. And I think asking qeustions is part of roleplayong so I think that gather info may interfere with roleplaying in some way...
**So, what's your opinion about it??
Actually, the more social skills are suppose to work in conjunction with roleplaying. Example would be Diplomacy. The skill takes a minute to use, so your characters have to roleplay around trying to explain things, or make amends or whatever and then roll a diplomacy check to determine how the NPCs react.
I don't know what rolls are suppose to be hidden and what aren't, as I let all my players roll their own rolls, even hide and move silently (since in 3.5e, even a low roll doesn't mean you failed), same with search, spot, and listen.
As for the Gather Information it should be used at the end of a small conversation where the characters have asked questions to determine if they get any useful information. Joe Nobody may or may not know the questions being asked, and thus Gather Information comes into effect, if they succeed he does know, if not he knows nothing or maybe a false rumor (the PCs don't know if they failed or not if you don't tell them after they roll, base your NPC's knowledge off those rolls.)
It has been noted before, and I agree, that Gather Info is meant to replace roleplaying dozens of conversations with an equal number of Joe Nobodies. When interacting with specific NPCs, roleplaying is the answer, but who wants to roleplay a day of tavern hopping and buying the local yokels drinks and getting them to talk?
You could emphasize that you'll use gather info as a "streetwise" skill. In other words, with out it you can wander around all night, buying drinks randomly and speaking to everyone-- or, with gather info, you spot the likely contact for the Blacksmith's Guild, have a quick chat, and get the information you're looking for.
Played this way, the PCs will always get the information they need-- it's just faster and cheaper if they have good gather info. That'd be particularly useful if they're tracking someone and don't want to fall behind...
It should also be noted that if the PCs are trying to track down someone in an urban setting, Gather Information is the replacement for Survival when tracking (via the Urban Tracking feat).