The F250s are a great TV. Congrats.
We upgraded from an F150 to an F250 a couple of years ago. Have a TT with basically same wt. & length. Until you have personally towed with a 1/2T and 3/4 T, it's difficult to appreciate how much better the 3/4 T is or to explain it to others. For us, the difference was black & white (groan).
I spent 20 years living in Saanich. Looks like the 2nd pic might be in the school parking lot on Sooke Rd? Sure miss the Island... Very fitting that you have an "Island" Trail TT too. ;) Would dearly love to do a camping trip to the Island but the ferry fares are outrageous.