I don't know the radio systems in your part of the country so I don't know if you need a digital scanner and/or a trunked scanner as well. I have preferred the Radio Shack and now GRE scanner brands for quite some time now. I have some Unidens still in use. If you are only going to have one scanner make it a hand held. There are some disadvantages to a hand held and it is nice to have mobile/bases for the cars and home, but with a hand held you can travel and use the radio in motel rooms and at the homes of people you are visiting. You can also take it to sporting events and concerts and can often pick up radio traffic for the event that can be useful.
If you travel and would like to listen to radio systems in big cities where there is increasingly trunked and/or digital radio systems, I would recommend you buy the PSR-500. This is a very good radio, but with a more complex learning curve when you first get the radio and try to program it. The best thing to invest in is software to program a radio. You can keep all sorts of files for different areas of the country and manually programing the radio is difficult because of all the buttons you have to push and the difficulty of making changes to the program. The PSR-500 has 21 "Virtual" programs or files with a huge capacity. If you have the Starrsoft Software and a subscription to this site you can import the information from entire radio systems into the file you are writing for the radio.
The newer scanners also have the capability to operate in the narrow band mode. At present all federal radio systems have to use narrow band, however, more and more state and local systems are starting to use it as well. State and local systems have to switch to narrow band by 2013. If you buy a scanner that is not capable of narrow band operation right now it will become increasingly difficult to use as 2013 gets closer. The main problem with mixed narrow band and "wide band" scanning is that the narrow band signals have a decreased audio level and when the volume is turned up to listen to narrow band, the next time the scanner lands on a wide band channel it will blast you out of your seat. The PSR-500 has the ability to program an audio boost for narrow band channels and it levels out the audio output so this blasting effect is substantially reduced.
In the long run it is best to buy the most expensive scanner as it usually has features that will be needed in the future and when you buy lower cost radios you have to replace them far more often, thus eating up any savings you may have made by going cheaper to begin with. However, $500+ for a scanner is a hard pill to swallow and you have to figure out what it is you are going to be listening to and how likely a change to newer technology such as digital and trunking is possible for the radio systems you are interested in. A cheaper radio will not do well once the narrow band mandatory switch comes in 2013. Replacing the cheaper radio in just 4 years is probably in the cards.