There are a thousand reasons to keep and escalade and not use it for towing, but driving dad's caddy on Sundays may be the most important one

My Dodge is a 4x4 4 door. It has a built in "Jake Brake" which will really help slow down the load without touching the brakes themselves. I did have to buy a 4 inch drop hitch in order to get the trailer level. Now towing basically the same boat driving my buddies Excursion with a 3 inch rise hitch there is still way to much tongue wieght which makes the front end squirrelly. Also the fuel mileage, I get 17 unloaded and 13 towing in the Excursion my buddy gets 14 unloaded maybe 8 towing. Now his Excursion is the gas V10 so I would guess the diesel would be better.

He left me something else for that.....wish I could post a pic.

I towed my 288 with a z71 Tahoe and hated it. I moved up to a 3/4 diesel and loved it. I now have a 32 and couldn't imagine ever putting it behind a half ton. Loaded and fueled a 32 will be knocking 10k

You can, upload to photobucket first, then copy the image link and post here

Pretty much covered here already.
But assuming you have a 32SS with the deeper hull (not the older Dominator which is a fair bit lighter); you absolutely need a 3/4 truck. The Excursion fits that bill, while the Escalade does not.

Sorry-Sierra Denali

I tow my 32 with a 2014 F350 diesel. Hardly even feel the boat.

I thought the weight difference was like 400 lbs and 50 gallons of fuel.

Your buddys Excursion a 2wd gas? If so that explains the not so stellar towing with the rise hitch. My diesel 4x4 Excursion uses a 2" drop, no issues.