Sam,
I've grown uparound the water, but unfortunately, we've never been able to get a boat, instead we have 3 seadoo's haha. Last summer I bought my own wakeboard after bumming off of friends, and the seadoo's all I've had to ride behind. When we go out with friends the parents anchor the boats and the kids ride behind the Sea Doo's in the cove all day. They pull great, the wake just isn't there obviously.
From the driving aspect, the boarder does tend to tug the back end one way or another just a LITTLE, but it's really not a big deal. We have a GTX, LRV, and a WAKE Edition. The LRV and WAKE edition have 155 HP and the GTX is a '94 so i know the HP isn't very high at all. I'd imagine the 110 you were speaking off would work fine.
If you decide to go with something more than 110hp, the LRV's are no longer made, I believe the last model was out in '02 or '03, but they put out a bigger wake (not quite like a boat but its something decent, and it has large rear compartments that can be loaded up for a somewhat larger wake). It also is a 4 seater so there's added weight/more room there. The wake edition comes with two wake racks on the sides and a rear pilon that raises up about 3 or 4 feet(not extended out in the pictures below) from the back. Honestly the wake differential isn't big between WAKE Ed. and the LRV. Sry for ramblin' haha but I know wat it's like to not have a boat (hopefully that changes as soon as i get a job out of college)
here are picks of the wake edition, and me riding behind it, from this past weekend.
(sry about I cut so much out, the file sizes were too big)