I personally wouldnt buy Air ride just because its another part that can fail (and it will) when it does i wouldnt pay all that money to replace it and id end up swapping to regular suspension anyways. So skip the step and just go with regular suspension, maintenance free as well. I think its honestly pretty cool and convenient, just wouldnt personally put it on my truck. There is quite a few threads out there about the air suspension you could read on. Its a 50/50 really. The people that have had it for 4-5 years they love it of course. Got people that had it for a couple years it failed and they swapped to regular because the price. Got some people that it failed soon and they hate it becuase it had nothing but issues. Just a subjective opinion really. I just choose good ole regular suspension. Just easier to deal with.
The heaviest im towing right now is my 26ft Eliminator boat. Dry im at ~5900ibs. Filled with gas its another ~300ibs (50gallons) so ~6200ibs. Plus gear/tools lets just say 500ibs to over shoot. ~6700ibs total. Not much for the 2500 but the way the trailer/boat sits (even after Timbren bump stops) in my 1500 it was struggling and i was getting thrown everywhere when i hit any bump, to the point i didnt even feel safe with my wife and son let alone any other passengers, it was a slow drive. Drove the 1500 about 4 times to the river and got rid of it after the 4th drive when my wife actually got to feel it and she gave me a look like "damn you werent lying about upgrading trucks" she thought i just wanted a new truck for the hell of it.. So upgraded for safety, plus we have desert toys so a toy hauler is coming in the near future and the 1500 wasnt gona tow anything close to the size trailer my wife wanted, we would have had to really settle which is what we refuse to do. So we decided on upgrading to 2500, just like you, alot of money was spent so we did A LOT of research. We thought about a 3500 to just wasnt logical for us and will never tow that much. went down gasser vs diesel as well. Just found what worked best for us and will keep this truck forever or atleast till it doesnt make sense to keep or fix it anymore many years from now.
Bumper pull.