I noticed something last night when I was uploading POIs to my Nuvi 200 with my Mac and my roommate's PC.
The Mac beta version of the Garmin POI loader allowed me to keep the subfolders and the POI files I sorted in them working properly. Then I used the PC version of the loader so I could mess around in manual mode to set the alert distance for the Redlight Cameras (since the Mac version doesn't have manual mode, sadly), and the POI files in the subfolders did not work. Whenever I selected the end POI file, it only listed one location.
I am happy to live without the manual mode if it means I can keep the folder structure, but it would be nice on a future update.
Not sure what you experienced, but the PC version of POI loader does support folder structure. You point to the main folder and all POIs will be loaded with a file structure representative of the folders and 1st level subfolders.
The Mac version is BETA... I'm sure it will end up with the same features as the PC version when it's done.
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