A Highlander is more of a mid-size.
Just a thought here... are you going to feel up to hooking and unhooking a trailer? Have you considered a motor home? There's a 10 year old, 24' Class C with 40K miles, Ford V10, for sale an hour from me for under $25,000. Seems like with that much depreciation out of a unit by that time, they can be pretty affordable. And no unhooking, other than your water hose and electric cord.
Why are some folks high on pickups? I think mostly because they have a longer wheelbase, which makes towing more stable and secure than a shorter wheelbase, full size SUV. But a midsize unibody SUV like the HL actually tows very well in terms of handling and maneuverability. They are low to the ground and not tippy, so you can swerve to avoid things more readily. But I would not want to tow more trailer than what I have now with my HL.
