I/O to Inboard conversion

Has anyone ever done anything like this before?

We have an older I/O, 18ft powered by a 350 Chevy (320 hp) that was possibly converted from an outboard at some stage, but I'm not sure.

Last night I discovered a major oil leak, oil in the bilge and none in the engine. I'm not sure where it is coming from, under or behind the engine somewhere probably which basically means we may have to pull the motor to fix it since there is next to no room under there. I'm pretty gutted we've only been out 2 days this year and we have another massive fix to do now. Seems like we fix this boat two or three days for every one on the water.

The stern leg isn't in the best condition and will probably be quite expensive to rebuild. The power tilt has never worked because someone burned out the pump before we bought the boat. So the advantages of having an I/O pretty much don't exist in this boat any more.

I am trying to figure out if it makes sense to convert to a V drive, and also find out if there are any pit falls to watch out for, or any good advice out there. D drive might be easier but I don't want the motor in the middle of the boat. We would need a new trailer but our current one is pretty rough anyway and sucks for towing on the open road, so it would be nice to get a new one.

The wake is almost like a CC2001 currently, solid and steep. As a V drive I think this wake would be incredible. This boat weighs a lot dry, about the same if not more than a modern 21 foot wakeboat I'd imagine. We rode on the weekend with 8 people on board and no additional ballast, the wake was nearly knee high and clean 70 - 75' back at about 22 mph. Not bad for an I/O.

While this is not really a project I want to start in the middle of Summer we can't ride with no motor so it would give us a chance to pull up the floor and replace at least some of it, as well as fix the leaks in the front ballast tank and maybe add some new ones and new more effective scoop plumbing. Plus I can look at fixing some cosmetic things that have been ignored for a while and change out the stereo that doesn't work for one that does.

After a quick search this morning finding the V drive might be the big hurdle as I couldn't find any used ones for sale on local auctions, although we might find one new somewhere. I will also need a transmission if I want her to go anywhere when we're done but I don't know anything about what kind or size.

Anyway, I'm just looking for advice at this stage, all comments welcome. I'll get some pictures some time soon.