Check this
Garmin nuvi comparsion chart to see what's included with the various models. We're in SamsClub every other week or so and I don't believe they've had any nuvi's with lifetime map updates. The 265WT model you mention includes "lifetime traffic updates", but since it uses MSN Direct, "lifetime" runs out on Jan 1, 2012.
One can purchase a nuMaps Lifetime subscription for $119.99 that allow you lifetime map updates (for one device). (Note: if you have City Navigator NT and a supported handheld, like the 60c(s)x, you can purchase this subscription too.)
We bought a 255W from Sams back in August and have used it to to augment our 60csx for routing and caching. We also use a GSAK macro, along with Garmin's POI loader (free) to load caches (and the rest of the GPX data) on the Nuvi. There are other ways to load the data, but using the method above, allows you to load 1000's of caches.
If I were choosing between the Oregon and the 60csx, I'd go with an Oregon. While the 60 series is still in the model lineup, firmware updates are few and far between. On the otherhand, for the Oregon they are turning out fixes and enhancements regularly. See the
Garmin Oregon Archives (GPSFix) for more information.
As far as email/Win 7, you could go the gmail route for your gc.com needs or possibly access your current email via a web browser. For example, I can access my RoadRunner account and/or accounts at 2trux dot net, via the web, when we travel.