The 1996 show was great for what it was (I think so anyway) I still enjoy watching it to this day but I admit, done properly something newer would be pretty awesome too.
The idea has some merit, but honestly the best way to do this would be to handle it yourself with a group of friends. Forget the web show with a budget idea, forget Sci Fi channel ever caring enough to see it, just get some cardboard and set everything up in your garage or basement and have some fun. Use game footage for flight scenes, that's about the best you'll be able to do at this point.
Having the money to buy costumes, and makeup and all that would be lovely but just having a good looking show isn't having a good show. Costumes and such are only the beginning.
For a massive fan drive I would imagine you need someone respectable, dedicated and trustworthy to take charge of the project, and several people not only willing to act, but actually
capable of acting, this detail can set it apart from other web shows and catch the eye of say, the Sci Fi channel, as unlikely as that is.
On the other hand, just letting anyone who can show up perform could be more fun for everyone there, but probably wouldnt produce as satisfying an end result. Sure those involved would have the fond memories of playfully ribbing the guy who mispronounced "Kilrathi", but the audience would think "I'm not paying for/donating to
that!" if you're looking for a donation driven budget, its gotta be worth donating to.
Equally, if not more important, you need not one but a group of capable writers in order to produce a story that grips the interest of old fans and draws in new ones off the net. A good enough story can sometimes make people forgive bad actors (
sometimes) and most importantly you need time, money, and a place to throw everything together. Character interaction would be pretty shallow if it's just a bunch of people talking to their webcams and some editor splicing it together to look like two people in entirely different rooms are having a conversation face to face.
All of these people have to really love the work too, because lets face it, they're not going to get paid for it and most of them will have bills. I'm not sure how the Star Wars and Star Trek fans pull off some of the fan projects they do, some of them obviously have none of these things, but I'll bet most of the better ones probably have at least some of these things.
To me the best hope a Wing Commander series could ever have would be to gather the above resources briefly, compose a Pilot Episode, and send it to anyone and everyone who could possibly take up the show, of course for THAT you've got to deal with the whole copyright madness issue.
None the less I'd probably be one of the lunatics supporting it whatever form it takes, you gotta respect someone who'd spend the time and effort of making their basement look like a flight deck