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Personally I'd go with TomTom, especially if you are traveling and looking for hotels along the way.
I took my TomTom on a road trip from DC to PA this summer and it helped me find a hotel in no time. Actually helped me avoid a traffic jam too! man, that thing is the best co-pilot (no offense to my directionally challenged friend who was on the trip with me).
I downloaded Mullet Mike as my navigation voice and my mom said I am starting to talk like him
I just posted on another forum how much I love my Garmin Nuvi 360. it was a little over $200 from Amazon. I have used it for finding hotels on the road - just pull up the lodging screen and you can call hotels directly (via bluetooth if you have a bluetooth phone - I love that feature!) from the unit to inquire about vacancy/rates. It also really came in handy when traveling out west when gas stations were few & far between - if I was getting low on gas I could bring up the gas page and decide if I should top off immediately, or if more gas stations were coming up soon. Ditto food places.
I bought mine in June 2008 and I was able to update to the 2009 maps for free.
I chose not to get a widescreen as my car is small (Mini Cooper) and space is valuable!
I decided I didn't need the traffic/FM transmitter or MSN live. The 360 is a good basic, affordable unit. The only time I have had problems acquiring signal is in parking ramps - but again, I'm not in large cities that often.
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