I don't really try to name things. I just refer to them as something random until one day I hear/read/think a word or phrase that happens to remind me of the project/character/thing to name, and go "oh, that's what I can call it!"
For VNs/stories, I personally like to use names that are relevant but non-obviously; that is, I like to use the title to draw an extended metaphor, or emphasize an aspect of the story that's important but not super prominent. I'm very fond of using a recurring image or a theme as the basis of the name. I named Reset because the VN makes a few metaphors about resetting video games and computers, and while they occupy a small amount of text, they're significant to the meaning, so I used the title to draw them out and help encourage the reader to apply those few metaphors to the entire game. Another WIP about two people who meet via anonymous notes is called On Paper, which refers superficially to the unusual medium they meet through, but also alludes to the idiom "looks good on paper" and foreshadows that the stranger won't be quite who the notes made them appear to be.
It probably IS worth actually taking the time to think on what the title means and how it affects the reader's understanding. The thing about a title is that it's the number one thing (sometimes the only thing) a reader knows beforehand when going into a work. If that word/phrase comes up in the text, the reader is probably going to pay particular attention to the statement. It can be a great tool for directing the reader's attention and emphasizing a part of the story in a subtle way, if the title refers to something that's not mentioned often. If the title is something obvious like the name of a setting or character or key item, this meaning is lost, which is why I'm not very fond of that sort of title. On the other hand, having a character's name as the title can quickly establish the importance of a character, even if they don't DO anything important until later. I'm thinking this would work well for, say, a romance with one love interest, where you want to capture that the protagonist is fascinated with them from the start even if the protagonist doesn't actually get to know the love interest until later. You can also use titles to set up false expectations and emphatically destroy them; in a story with a major twist, the shock will be heightened if the new direction goes counter to what the title suggests, or especially if the title suddenly takes on a new meaning.
As for characters, I generally either stick with the first random thought that sounds good, or if I really want to name this character NOW, I'll search meanings related to some aspect of the character or name them after someone else who's relevant in some way. I do strongly prefer for major characters' names to have SOME meaning, even if it's a meaning only I really understand, like a Jackie who's named after Jack Kerouac, or Cairbe, whose name was a portmanteau of the name Cairbre and word cherub. By the way, making portmanteaus or modifying names is a great way to come up with names that are unique but not random.
I also like to consider the realism of a character having their name. If I know a character has traditional parents, I won't give them an outlandish name (or vice versa). I won't use a name with very apparent negative connotations (the sort of name that makes you go "who would name their child that?!") unless some sort of reasoning is given--for example, a friend's book contains a character named Nemo ("nobody") which is awfully weird for someone to name their kid, until you realize his parents didn't want him, and then the name makes sense.
PS, I'd like to point out that I adore the name Cyanide Tea (although I have no useful comments on group names).
:: Kura's VN Projects and ResourcesComplete Chasing the Sun
[a meditation on light] :: In Progress RESET
[guilt, love, existentialism, and video games]