If both went to sale, yes, but that's a big if. My strong impression from folk in the business is that most of these KS games do the KS, that funds a print run, and then that's pretty much that - possibly the designer gets future print runs to sell themselves or supply to independent stores, but increasingly a lot of these sorts of boardgames are on a "do the KS, make the game for the backers, move on to the next project" business model.
I think my rule with playtesting is that you always need more than you think, and that the more people you playtest it with, the more possibilities will emerge. I'll have a think about catch-up mechanisms - you're right, one would definitely be useful in this sort of game.