I keep asking myself what the hell is wrong with you people. Generations, First Contact and Insurrection were solid at the box office.
When those movies came out, nobody asked "is it too soon?". Nobody said "Are they too old?". Nobody said "TNG is the final nail in the coffin!"
You guys seriously should stop messing your memory up.
But I don't think we're talking about box office success, we're talking about quality. The movies (other than
"First Contact", in my opinion) were poorly conceived and I would argue that was natural coming at a time when the people behind TNG were burnt out creatively, as evidenced by the fact that so much of season seven was bad compared to the others (except
"All Good Things..." and a handful of other episodes).
Taking more time might have lead to the writers being able to relax long enough to come up with better ideas for movies, or possibly bring in someone new (i.e. Nick Meyer with the original movies) who would contribute a fresh perspective to keep those characters and their stories interesting in the big screen transition. Like I said, though, they didn't have as much time to delay the movies because of the cast's aging, so they were in a tough position. Do it right away while the cast is still young, or give everyone some time to recharge their batteries creatively, at the risk of the cast being too old by the time that's happened.