Congrats! I hope this boat works out.
The first thing you need to do, as far as the wet spot is concerned, is figure out precisely how big it is and what the dimensions are. Forward of the stbd chainplate, you can do the work from the bottom and the repair will be hidden by the hanging locker. Aft of it, though, you''ll find that part is above the cabinet that sits against the bulkhead, and part is exposed. It can certainly be done from the bottom, but depending on the extent of the damage, you may need to disassemble some cabinetry and do a careful job with the glasswork as some may be visible in the main cabin.
Fix it sooner, not later and, while you're at it, isolate the chainplate from the new core with thickened epoxy so you're not repeating this project down the road.
As far as going out with your currently non-sailing family goes, I think you'll be in fine shape. I sail often with just the wife or with non-sailing friends and I have little problem. If you have a roller furling headsail, then you'll find it that much easier.
Encourage your wife to be comfortable on the helm for the times when you need to go forward. Also teach her how to depower the main by dropping the traveler. It will help her get a feel for how to keep the boat on its feet and it will probably improve her comfort zone as she learns that she also has some control over the boat.
The boat also sails very well with just the main. I've had friends out for dinner aboard and, despite quite a bit of breeze, well were sailing easily enough to have drinks and food in the cockpit and were occasionally sailing above seven knots.
