Hi, I'm Nathan. Nice to meet you. (drinks)
I have a rowhouse in the city, don't have a 3-car garage, and my commute is precisely two miles, but for the sake of the hypothetical, I'll humor you.
If I had a "highway cruiser" it would definitely be a manual. Really, is there anything sexier than a nice, powerful sedan or wagon with a manual? For this hypothetical, let's say I would have a RS4 or CTS-V wagon with MT. Absolutely no way I'd consider buying an automatic in this case.
The highway cruiser described above would likely be as practical a vehicle as I would ever need. Furniture stores deliver, and I don't often buy huge things from Home Depot. If I do, they have pickups and vans for rent by the hour. But, let's say I did buy a truck. My roommate in college had a RWD Dakota with a 5-speed manual. With the lower ride height of the 4x2, it was a pretty stable, yet tail happy truck that was easily controllable with the MT, and was pretty fun to tool around town in. It could carry mulch or plants or anything else I could conceivably need. This or something similar with a MT would be my choice.
And, no I'm not just saying that. I really have no patience for automatics in any kind of vehicle. Maybe if I drove a city bus? (dunno)