Got my first wireless 2 days ago after getting gatvol of the wired ones breaking all the time.
So far I'm loving it, must still get used to not having to take them off if getting up from my chair and walking somewhere, the charging doesn't bother me yet, I just plug them in for a hour or so.
Depends on circumstances. If I'm really listening to music then wired. And it would be expensive to get wireless ones that equal my wired headphones. For background listening when I need to move around then I'll use wireless ones which are adequate, but only in cases where I can't just play music through decent speakers.