Squat is going to be dependent on the rear springs, so you'd see decent squat unless you throw in airbags, add a shackle/spacer lift to the rear leafs, or replace the rear leafs altogether. My towing has been rental trailers, so nothing consistent weight wise and i never measured it.
I'm with you here, that seems like you're pushing your luck. If it was staying local that would be one thing, but proper road-tripping with that much trailer on that small of a truck sounds like an accident waiting to happen...
Discount Tire for life! They gave me a loaner set of tires for a weekend so i could go visit family while my new tires were on order. I'll never go anywhere else.
So I initially went the rear shock upgrade path, and man was I happy with that. I had the factory fx4 up front and scored a used set of Fox 2.0 rears. The bouncing was gone, ride was much more compliant. Fox's are on the softer side, and do require periodic maintenance but I've been very happy...
So I ended up going the OEM route primarily because the aftermarket ones all hang down which isn't a good look in my opinion, the OEM tucks up nice and tight (but is a pain the butt to install)
Good looking rig! I think most people just do a small puck spacer on these to level them out.
https://fordrangerlifts.com/shop/ols/products/2021-2022-tremor-level-lift
I'm not even sure if the Tremor rear shocks fall into the 2.0 category, at a glance they look more like monotube shocks with a reservoir... You also wouldn't be able to level your truck out with just the tremor shocks, they all have a bit of factory rake so you'd still need a spacer or something...
So one thing to consider with a rack like that is if you have a more unique frame shape, that style of top hold down might not work well. I would look at the 1-Up rack i linked previously, its rated for bikes up to like 60 or 70 lbs so plenty for any e-bike, and has arms that hold the wheels...
Thats not going to fit without pulling wheels off... I have a large Transition Spire, so probably roughly the same overall length... I would highly recommend getting yourself a 1-Up bike rack. They're spendy but its super solid and holds my bike in place despite going over speed bumps at like...