MACS I just did all the homework on Garmin and bought a nuvi 255W for myself from Sams. A week later I went and got one for my dad.
On Garmin nuvi 2XX series the W means wide screen (a must in my mind) the T means traffic (in your area maybe a good thing not so much in mine and I can add it later.)
Lets start as you go up from the 255W to the 265WT etc. You add traffic and blue tooth (ie speaker phone and ability to dial points of interest when phone number is included). I didn't need either.
Down from the 255 means you get turn by turn directions announced WITHOUT voiced street names.
To me the 255w hit the perfect sweet spot voicing street names in the turn by turn instrucitons yet not making me pay for traffic and bluetooth (which you presumably already have in your car.
Traffic may be pretty cool and you may use it more in your area, but as I said it can be added later (but cost more to do so). Traffic seemed to be the only complaint on the nuvis because it either was too slow to help or the adversiting pop ups were annoying(yes they give you free traffic but also send adds to the unit).
I got my 255w at sams for around 160 a few weeks back. The 265W on the place named after the river and hot athletic women is at about something like $215 (too lazy to look again).
The reviews of the 255W at the river place tell the story. Awsome unit.