Let's ask another question here. How do you plan to use the scanner? Will you carry it around in your vehicle or will it sit at home on a table top?
One of the major disadvantages to RS scanners (and many earlier Uniden scanners) is they only allowed you to program ten banks. You may have 1000 channels, but you could only track ten trunked systems*. The newer Uniden (and the new GRE's coming out next month) allow for dynamic allocation, you can have more than ten trunked systems.
Right now there are not that many digital systems in the area. On the southside, it is Chesapeake and the two Navy bases (on 400 MHz systems right now). VSP is slowly putting out their digital replacement STARS system (actually, STARS is SUPPOSED to be all state agencies, but there are some problems with the system, see the thread on STARS problems).
All in all, I'd say you really need to be looking for a digital scanner, especially if the scanner will be mobile. Living close to Chesapeake, I'd seriously consider digital.
So as the PRO-96/2096 (handheld/tabletop) does not cover MIL-AIR, you need to start looking at Uniden or the new GRE.
Tough decision, but there is enough experience on this board to help you make the right one. Above all just don't go jump into something. Think it through, ask questions. When you are getting ready to spend a couple of hundred dollars or more, there are no stupid questions.
Non digital scanners are less expensive, but then you cannot monitor digital systems (don't mix digital with encrypted, York County is digital with encryption). So sit down and set your priorities. What do you want to listen to the most. Are they digital or analog. What are your secondary systems. Then shop around to find a scanner that will fill your needs. No one scanner is perfect, find the one that best fits your needs. I don't listen to MIL-AIR, so for me the 96 would be okay for you, it would probably be a no go.
*The reason you can't have more than ten trunked systems in the earlier trunked scanners is they will lock onto the trunked system control channel. First come first served.