First, listen to your wife. They're always right. (I learned that lesson long ago and sometimes even remember it before she reminds me).
I can't help you with the Pilot decision really as I don't have any personal experience with them. I have towed boats and horse trailers for many years, and worked on cars for a living for about 15 years in a previous life. Transmission work on todays cars is so expensive you could probably find a used truck for less than a transmission job would cost on the Pilot. Food for thought. Going a little over the towing rating of the vehicle for short trips would probably not be a big deal. If those trips have hills in them, you might want to reconsider. I've always been a fan of a full frame to attach a hitch on, for a towing vehicle for a boat the size of a 260. Also, if you trash the tranny, your wife will definitely be right. Do you really want to go there?
I say, buy the boat and figure out how to tow it later

My 2 cents.