Nice trailer! You are right, it looks like a great match for the new Tundra.
I have a 33' overall length trailer that I towed with my 2005. I just got the 2008 in Jan and have only towed the trailer from storage to my house and back.
I can't think of any issues for a trailer this length. I started with a pup, then a 24 ft hybrid travel trailer and now the 33'. The only difference is making sure you have plenty of clearance in turns.
Get yourself a nice WDH, a good brake controller, set them up correctly and then enjoy the tow.
Tom
