Ed, if you are concerned about up-to-date map data, and accuracy of map data, in my experience any product based on maps licensed from Navteq is very good. Microsoft Streets and Trips does use Navteq maps. But I would suggest to save yourself money, and not buy the "Connected Services" version at least till Microsoft starts advertizing traffic coverage in your geographical area. The Connected Services version is not even sold in Canada, yet. The coverage is officially available still only in the US, even though recently it started to work in three Canadian cities: Vancouver, Toronto, and Montreal. But even here in Toronto, only a short segment of only one highway is showing traffic flow information. As of today (Nov. 2007), it would still make no practical sense to use this service in this city. Instead of buying the most expensive version, buy just the software w/GPS receiver version, or buy the software, and then use some other compatible GPS unit with it.
You mentioned Garmin and Tom Tom. They both make excellent products, but they are mostly in the PND (Personal Navigation Devices) business. Tom Tom has no product for laptops at all. The only way to use Tom Tom on a laptop would be to run their PocketPC version on an emulator.