On my 2500 stock was 285/60-20, I had planned to replace wheels, possibly drop to 18's, but decided to save the money and stay with the stock 20's, I actually think they look decent enough on my truck. So I went just slightly larger to 285/65-20. I really like the difference, my wife doesn't mind the slight increase in height mostly due to having the motorized steps. And I'm constantly climbing into the bed or standing on a tire to bungee stuff down, so I don't want a truck any taller. So I'm really happy, will stick to this size, no plans to level either.
I say all that as background, your sizing decision is interesting. Here's all the diameters compared. Your 295 choice is maybe 1/2" wider than the 285's I have.
285/60-20 - 33.5"
285/65-20 - 34.6"
295/60-20 - 33.9
295/65-20 - 35.1
I might suggest instead of moving to the 295/60's maybe go with 285/65's like I did. Just a thought.