I could write a novel on this topic.... I recently sold my 30' (bumper to ball) TT in hopes of getting something larger for the exact same reasons you talk about. I was about to put a deposit down on a unit out of state and make the drive but thought I should at least go look at a similar length unit. When I actually saw what 36' looked like versus 30' my jaw dropped. It's a BIG difference.
You have plenty of truck for virtually any TT setup with good WDH and anti-sway. That, with your extensive experience towing you'd be fine. To me it's more the camp spots and trying to find a place to put 60+ feet of truck and TT.
In the end I went with a 5th wheel and am trying to figure out bikes and other storage. I had one before and made it work so it's not impossible.... just a bit of a challenge.
My best advice is to physically go look at lots of different trailers and 5ths. Depending on how you use it a longer TT may be fine. I know just because something works for me doesn't mean it's for everyone.