How many people do you travel with? What's their approximate weight? How much stuff do you carry in the truck with you? How much stuff do you carry in the truck bed?
Essentially, you need something that has a cargo carrying capacity to carry all that, the weight of the hitch (say 250 pounds) *and* the pin weight (which is going to be in that ballpark, if not a little higher depending on what's in the TH's garage).
IMO, those kinds of numbers either need a newer SRW truck, but that'll blow your $30k budget or an older DRW truck.
To be honest, I don't drive much now that I work from home- but the dually isn't as much as a hassle as I thought it would be. Wife and I both do school drop-offs in it occasionally and that's about as cramped of a parking lot as it gets!