Checkered ---- I could wax on for a long time, but you have some major soul searching to do. I suspect that what ever direction you go, you will be happy. I have an "Antelope" in my garage and know that it would not fit those needs either. Things have changed a lot since you bought that bike 22 years ago.

First - A couple thousand miles is not a big deal. Most of the people on the list will do that many miles per year. The 400 miles you rode in the past month suggest you could easily do so also. That said, I sense that you would like a new bike, and I have found that a new bike alone has in the past enervated my riding.

If you like the upright style, then a hybrid will likely be fine. I suspect your Trek 830 is an older version of what is now called a hybrid bike. I don't have a clue what your LBS is calling a dual-sport bike.

I like the flexibility my cyclocross bike offers. Put on road tires and it works great on the road. Or, switch to more aggressive tires, and take it off road where it would be fine on gravel paths and the like.

So much depends on what your budget is. I have found it useful to think about how long you will have the bike, and dividing the investment by the number of years. The more you spend, the better and more fun the bike is likely to be....