Six original cast films seems enough to me - as they pointed out in TUC they were all getting very old, too old to be believable as active personnel. It is hard to make a new film in a franchise annually. Apart from anything else it takes pretty much a year to actually make a film, let alone distribute and release it effectively. That and the lack of "event" associated with the films would pretty much guarantee a series of flops.
I've said it before, and I may as well say it again. I'd love to see Shatner in the next Star Trek movie. I would for no other reason than pure guilty pleasure. If it doesn't show up though I'm not going to lose sleep over it. His involvement is in no way essential to my interest in the next film. The video I've seen before. It's a nice thought but a little intense in its intentions.
as a fan film, it's not bad at all. The only wrong step was to acknowledge Generations. There should be an exception in the canonability rules for that.
It's kind of hard to talk about bringing Kirk back from death without talking about the movie he died in.