Can I dream?

My two cents: I'm going through a similar issue. I started out with a Tahoe 3.5 ltr V8 with Max tow package, bought my first trailer a 28' GVW 6700lbs trailer. The horsepower was fine, but the sway wasn't. it only took one year before I upgraded to a 1/2 ton with Max tow package and a 6.2 ltr V8. It changed the towing experience from a white knuckle adventure into a stess free, relaxing ride. My wife and I now want a bigger trailer, since we have outgrown the 28'. Dealer is trying to sell me on a rig that's 33' and GVW of 8995. He says my truck can handle it. I posted on this site and got lots of good advice to weigh my truck first to get exact numbers since this was very close. I did and found out my truck would be just at or over the GVWR with that new trailer. Moral of the story is to get the most Tow Vehicle you can within reason of course. I guarantee at some point, you will want a bigger, heavier trailer. Since my truck is in great shape, we have decided to downgrade our new "dream" trailer to something lighter. Just need to find it now!