I'll weigh in as I am wondering a bit about towing as well. Below is my experience and I am open for advice/suggestions.
I have a 2017 4Runner SR5 Premium 4x4 and for my typical trips it is fine, although I am only towing a 195S. It has a 5klb tow rating and my boat weighs, per Yamaha around 3,200lb on the trailer. Figure 250lb for a full tank of fuel and around 550lb of gear and I am sitting right at 80% of the rated capacity. We did look at a 21' boat and one of the reasons I chose the 195 was the weight.
For the vast majority of my trips I have been really happy with the 4.0L's ability. Its no powerhouse, but I have been to Lake Burton in the N. Georgia mountains and regularly make a 30 mile run to either Lake Lanier or Lake Allatoona. I can definitely tell its back there, but I don't feel like the vehicle is struggling, just working harder. The one trip I have done that I felt uncomfortable was Coco Beach, FL which was a little over 500 miles. The truck was fine for the stop and go of any side road and trips around the beach were easy (flat). However, on the highway I felt like the vehicle struggled in 5th gear, so I mostly kept in in 4 and just stayed around the 60mph mark. Makes for a longer drive and got about 12mpg on the way there and back. My next long trip is coming up and we are going to drag the boat with us to Port St. Joe, FL for a week. I am going to try a few things to improve the long highway towing, but honestly it is something we may do once a year, after this year of course.
The 4wd is great if you get a slippery ramp, but I haven't had to use it yet. I do use 4wd low to back up my steep driveway. I think the articulating keel misses the concrete by around 2" when we pull out or back in and if I have gear in the back of the truck, I usually scuff the bolt on the bottom of the ball. I plan to add the airbags to the back of the 4Runner to help with the sag. It has gotten worse since I fist started towing with it, not by much. I also think it may help with highway comfort. I also want to explore switching out the Chinese Carlisle bias ply trailer tires with a set of Goodyear radials. Another option might be to add an auxiliary transmission cooler. I would love for the truck to have a set of 4.10 gears, but the next available ratio for us with 5th gen 4Runners is 4.56 and I think that would be just a little too steep for comfort. Honestly though, I will probably just hang in the slow lane and chill at 60mph.