Hi again,
"...my department is in the city about 2 miles from the repeater..."
Great, that's exactly what can be expected under average conditions. Remember that a repeater is located in the best place possible, on a high building, broadcast tower, mountain, etc. and often has several satellite receivers around the area connected through a voter which selects the receiver having the best signal. With a powerful (up to 250W) transmitter and high gain antenna at high elevation and a receiver nearby the portable the system overall works great. The same can't be said for you since "your milage may vary".
A rubber duck is great for a "walking portable" but hams have another definition of "portable". One may be simply a hand held or anything up to and including a "big rig" connected to a battery, generator or other power source and any kind of antenna system that can be set up and taken down easily. That should give you some ideas about portable operation, the equipment fits the need.