See
viewtopic.php?f=5&t=69117&p=739437#p739437 for our experience towing with the EcoTune and the stock OEM torque convertor.
Thoughts:
1. I think you need to give a little more thought to actual trailer weight. While this looks like a nice light rig the 2,725 dry weight is going to go up pretty quickly. For example a full 27 gallon load of water adds 216lbs then there is gray water, propane, clothes, food, cooking gear. I'm sure others that actually trailer this kind of rig can estimate better than I but I'd bet your actual tow weight is going to be on the order of 3,500 lbs.
2. 3,500lbs is well within the vehicle's capacity and others have towed a lot more long distance so I wouldn't worry about it.
3. you might want to check with Keith about which tune to get although I think you would be ok with either the EcoTune or the Full Torque EcoTune.
4. best I can say on your torque convertor is it will hold up until it doesn't. By that I mean if you back off when you experience shudder, trust me you will know when you do, and don't flog the power while towing too hard the TC should do just fine. But if you start having shudder problems a lot of the time then best upgrade to a Euro or SunCoast TC. That said unless you have the $s just laying around I would not proactively replace the TC as it may last for years but I would keep in mind that a replacement may have to be done.
5. if you tow a lot I'd shorten the transmission fluid change interval and if it's in high temp areas I'd consider a tranny cooler a worth while addition. If fact the latter is probably a better initial use of just a few $s than worry about the TC.
FYI if running in cruise we found that adding a bit of throttle before starting a grade made a significant difference in whether or not the CRD would have to down shift on the grade. No surprise there as cruise is "reactive" not proactive (e.g. it cannot look down the road ahead and anticipate the need for extra throttle)