Couple of questions...

Q#1. Mine doesn't do what you describe. My 260 brings up cities starting with the one closest to me (which happens to NOT be the town my mailing address is in - in fact it doesn't show until the 2nd page). I guess if you are near a state border, and the closest city center is across the line, that might explain it. It goes by line of flight to the coordinates that are in the database for that city.

Q#2. The only time that the map POI's are updated is when the entire map gets updated. That only happens with Garmin once a year, and it typically costs about $70 for the update. If there are specific stores or places that interest you, then the best thing you can do is download or create for yourself a POI file for it.

Here is how the city thing works. Type in Greenville and you will probably get "Greenville, AR". What it is doing is finding the match alphabetically both by city and state. So, for an example, you put in "Green"

Greenboro,TX would come before Greenville, AR because "b"oro comes before "v"ille. If it is the same name, such as Greenville,AR and Greenville,NC, then AR comes before NC

Hopes this helps.

...he's talking about using the "Cities" button on the "Where To?" menu. When you hit the button it immediately starts bringing up cities by proximity to your location. Only after you start to spell them will it work like you say. When you hit the button it will bring up the city with the closest coordinates to you, regardless of state boundaries, and without alphabetizing.