No question, I would do the inboard project. You have much less expensive re-power and, typically less fuel consumption. The major differences are; transmission, rudder, stuffing box and, propellor shaft/strut. Yes the engine takes up the enitre console and, you have more draft, but the bulk of the weight is now in the middle of the boat versus one end. An inboard does ride better. Parts are less expensive for the motor and, any automotive machine shop can re-build one. Also, if you have a GM bellhousing on your transmission, a Peninsular 6.5 diesel is an option. A 22.2 diesel? Wow, it just couldn't get any cooler. The only thing I don't like is how Aquasport did the fuel tank on the inboards, it's basically a big aluminum box up against the transom. It seems like there's got to be a better way to do it.
It came down to crab ropes for me. I run an amateur crew at times, and stuff happens. A rope around a prop is much less of an ordeal on an outboard.