Boats are so dumb Gary...
Honestly, get you some big wide sit-on roto-mould kayaks to start with. You'll be able to launch them straight off the Skeeter Shack lawn, and assuming you and T don't have upper body rigor mortis, the power plant will always go. Sure, you'll get a damp butt, but they're light, inexpensiveish and easily put back away if the weather changes, which it will.
On the other hand...Cheap, older power boats have very high potential for rot in the timber that hides inside the fibreglass, its almost guaranteed in the transom in fact. Also, despite the inherent reliability of the two stroke design, old 2M outboards do not like long spells between use and can be total a-holes to start on the wrong day.
Additionally, nothing kills a marriage faster than a poor launch or retrieve session. If your ramp (dock?) does not have good floating pontoons and wind protection, then someone is going to get a wet arse and risk the boat blowing over or away from them, if they are lucky enough to be the one who can't back a trailer. Yelling and refusal to participate nearly always follow.
Ease in bro. Nothing beats a great day on the water, but they are few and far between, and a lot of prep goes in to making it as seamless as possible.