How big is your direct drive? Just judging by the pic and the step over bow, you're probably in a pretty similar class to Malibu's Response LX. For those that want a smaller DD and don't mind the step over, the Response LX has a pretty great reputation already in terms of wake/boat quality and I bet wouldn't be much more than $40k for a new one if you get a decent deal. You can get one only a year or two old for low-mid 30's (and I don't think they sell very well, I've been looking at a lot of the same listings for a while now). Eg:
http://www.ski-it-again.com/php/skiitagain.php?topic=Search&category=Comp_Boat&postid=17409 . So I imagine your price would have to be pretty competitive with that kind of model. I'm not sure if 40 base plus options would work or not.
For ski boats, there is a lot of discussion that might help you here:
http://forum.ballofspray.com/discussion/4222/another-player
http://forum.ballofspray.com/discussion/4424/rumors-of-mastercraft-bare-bones-slalom-boat
I can tell you I was recently in the market and if there had been a player with a boat that could be had at a price that begins with a 3 that had a reasonable set of skiiing focused options (ie not
bare bones, but pretty lean), I would have given it a lot of consideration, especially if the reputation for the wakes was good at longer lines. It would still have been a tough choice though between that and a pretty well maintained & optioned used boat from one of the big 3. I'd have been looking for a true walk through though so it's a little more usable with the family. I was really looking at a Moomba Outback initially but those prices are creeping up too and by the time it was over $40-42k (which doesn't take much in the way of options) it just didn't make sense compared to a promo boat. I eventually settled in the mid-30's on a really well optioned, low hours 3 year old boat.
On your v-drive, does that rear compartment only open from the platform? Hard to tell from the pic but looks like it might be that way. That would be a big turn off to me. It's bad enough on something like the Response LX but that's a ski-from-the-dock type boat so you might not need to get to the storage all that often. On a v-drive that's a lot different if you're out on the water all day.