Gooseneck will work fine w/ a 2500HD. I've seen it many times with 25'+ trailers.
R
I've seen it many times also but it also greatly increases the risk of things going wrong. I've seen many bad accidents from this on the way to pismo and glamis in cali with this kind of combo. We've also had a few things like this gone at work. Most likely Jon, who is a careful driver, would be fine but like I said increased risk.
R