Since you asked for real life experiences I'll tell you mine. I have a Sabre 33ckts with a pin weight of around 2500 pounds. I haven't towed it that far to date, around 300 miles, but no problems. tows and tracks like a 5er should straight and true with no sway. In July we will do a 500 mile two state trip. I'll know more after that, but so far so good. I drive a Ford F250 Crew Cab 6.2L with 3:73 gears and love it. We are weekend warriors with maybe a week or two during vacation time so the 250 SRW is all I'm going to own until it gets to be time to start to travel more. Then maybe a F350 DWD but I hear tire and truck companies are working a something called super singles for commercial trucks. If that is true non commercial will not far behind. Time will tell.
-BC-