If you're towing I would definitely go with 4.56s especially if you're considering 295s. I tend to recommend lower gears since I went with 4.56s for 33s on my 96 and now I'm going for 5.13s. To me low speeds need deeper gears.
To me 3.73s are ok for 31 inch tires and smaller. My 2000 feels like I removed a pair of cylinders climbing a hill now. Gears will never damage a transmission and towing at low speeds will actually help. More torque multiplication means less throttle with means leas gas burned.
Well i went to a shop and they offered to do the gear change, labor was 700-800 i was like wow then I went to another shop I know the people at and they offered to do it at 299