Before reading on please realize that I tend to over engineer when it comes to upgrades. I hate to be left stranded.
For future reference in case the op decides to go for the boost. The weak point in your trans is cooling capacity and the torque converter. Lookout for a ballooning converter, especially if the trans hasn't been rebuilt. The rest of the guts of the trans should handle the towing, power and then some but I would drop another 500 - 1000 on an upgraded converter with the stock stall speed or a bit lower. Going lower will actually give you about the same stall you had before thanks to the higher torque from the supercharger. This will help keep the heat down in the trans when under load. More slip from a higher stall = more heat
I would consider upgrading the stock trans cooler or adding another one. I would also add an inline thermostat to allow the trans to heat up to operating temperature before kicking in the trans cooler. Too big of a cooler can cause problems too it if doesn't allow the trans to come up to temp.
Then the weak link will be your rear diff. If you have a limited slip expect those clutches to be the next thing to go but if they do you'll be fine. You just won't have limited slip anymore. If that happens then think of it as an excuse to upgrade!
It is unrelated but there is a chance you have a "combo" block in that truck of yours. Slide under there and look for 4.8 5.3 6.0 stamped on the side. If it's there then congratulations you have an early rebuildable block which has thicker cylinder walls. If you have it then I really wouldn't worry about the boost but expect to replace a head gasket or two during all your fun