Ver Hey,
With this new info, it sounds like you could do it (just) with the 2500 although it would be very close. I hope you never get a larger trailer, or haul a couple of extra passengers or ? I just don't see the negative part of buying a 3500 SRW. If the overloads really bug you, take them out. At least you have 900 lbs more legal weight capacity. No, the world isn't necessarily gonna end if you are sometimes 50 or 100 lbs over legal GVWR, but why risk it? Just remember that if you ever need that extra 900 lbs capacity, getting it later will cost you thousands of dollars. My 2 1/2 cents worth.
Dave