You answered the big question—does your present truck handle the trailer well. Since it does, you’re good for now. So, my dually answer is “when you buy the next trailer” or “when you become uncomfortable”. The biggest problem with the 2500 will be pin weight capacity, not CVWR or tow rating. Running it a little heavy will only wear the axle out a little faster, not break it. Depending on how big you think that you might go with a trailer, you could consider a 350/3500 SRW size of truck. That will have the additional rear axle weight capacity.
