Great question, and of course there is only one person who can answer it --
Darth Vader.
Seriously, though, I think Gonzo, Kholi and Alcove offer some good words of wisdom. The answer is truly going to be personal for everyone.
Me? I just
had to make one. I didn't give a damn if I was ready, I needed to do it. My case was kind of a weird one, though, in that I didn't make my movie with any intent of turning a profit. For a feature film, that's weird.
My next feature is definitely going to be a for-profit venture, and I agree with both Kholi and Gonzo -- there's gotta be some money there. I don't know if it's coincidence, or if there's something to the number, but like Gonzo, I've also set $50K as my absolute bare-minimum for the next feature production. Needless to say, that's a miniscule number, when compared to most feature productions, but I think I can make a quality product, and turn a profit on it.
Should you continue making shorts? I am. Not all the damn time, but I kind of just have an itch to do it, and I gotta scratch that itch every now and then. Plus, there's no question that there is something to be learned with every new production.
I do have one opinion on your situation, for what it's worth. I think you'd benefit by doing a couple more shorts, not so much because you need to learn more, but because you'll be able to network with more people, and perhaps get some more quality talent. Though I didn't comment in the thread, I did watch the behind-the-scenes footage of you doing the walk-through, and it seemed clear to me that you're working with untrained actors. I think most professionally-trained actors would be mildly offended by the way you sort-of force-fed their performance in that clip.
I don't say that as an insult, because I am in fact one of your biggest fans, and I also have been in the same place. I'm just saying that I think you'll find it truly liberating when you're able to cast some more professional-quality actors who will be showing
you how it's done, and all you have to is subtly mold and contour their performances.
So, I'd say maybe just a couple more shorts, keep networking, especially with actors, raise that all-important dough, and you'll know when you're ready. But don't forget to consult Vader.