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Did you mean nuvi 500 or 550 instead of nuvi 50? I believe the old nuvi 5x0 series (circa 2007) is the only road navigator Garmin has ever made that was geocaching friendly. If you truly meant the newer nuvi 50 (circa 2011), it was an entry level device and did not have any built in geocaching features. Any modern Drive series unit would have a much richer feature set than the nuvi 50, but would still not have specific geocaching features.
The GSAK macros that install the Geocache data on a nuvi device convert the geocaches to detailed GPX entries and install with Garmin's POI Loader program. That should still work fine on any of the modern Garmin road devices. I have used it on my 2013 nuvi 3597. The only thing that may not be acceptable is the way the modern devices decide to display (or not display) the custom POI icons while navigating. On my 3597, the geocaching icons do display while navigating in 3D mode, but the ones installed by GSAK are very tiny on the 3597 screen. That is OK for me, but some folks may not like it.
No nuvi models would use Galileo … they are too old.
I have to agree that the smaller icons are a huge improvement. Much better, but still not as good as the old devices like the 7xx series. I never could figure out what Garmin was trying to accomplish with those huge ugly icons. I have yet to read a post from anyone that likes them.
We briefly discussed the week rollover problem a while back in this thread: http://forums.gpsreview.net/discussion/comment/208489. The consensus seemed to be that Garmin had addressed this issue in most of its modern devices.
To see the hidden .system folder, you need to change your 2595 from the default MTP mode to mass storage mode, and of course change your computer folder settings as Boyd said. Maybe you have already changed your device to mass storage mode but I didn't see from your post that you had.