Silverado 1500... Enough?

If you're buying new, I would look for the truck with the highest rated payload/towing capacity. Dry weights don't mean anything and you will run out of payload quick. I don't know about Chevy or Dodge but I know certain fords have increased payload/towing packages. You mentioned that if you stepped up trailers you would step up trucks, is stepping up trailers on your mind? If so, I would buy the 2500/250 now. I drive a 250 everyday for my daily driver and wouldn't change anything. I think you will find that the gas mileage between the two trucks isn't that far apart. You will get a number of responses, from basically I tie my 35ft trailer with a Toyota Tacoma to you need a 3500 dually to pull a popup so just be ready. If I were buying a new truck and thought there was a chance in the next 4-5 years of buying a larger trailer a 2500 would be a no brainier. But to answer your question, the truck you're looking at should be enough, but it all depends on how much stuff you pack in your truck and trailer.