Anyone regret trading up

We have changed trucks as our needs grew but the needs sometimes grow because you think you have enough truck. Have had 1/2,3/4,and currently 3500 DRW diesel for our current fifth wheel . Our next change will be because the capacity of the newer trucks is so much greater right from the factory and we are moving to TC shortly so instead of big towing numbers I am now looking for big payload numbers , the current 3500 diesel 4x4 is a 2007 in great condition but has low payload numbers it pulls a 16k fifth wheel great but will be overloaded buy a large TC. like the original poster I lalso hate to part with my current 10 year old truck but I need more payload capacity so that's what's driving me to part with a perfectly fine 10 year old truck with about 60k on it .
Goood luck with whatever you do
Mike