@BBeast
That link to the Garmin map store is for purchasing 'out of area maps', like if you have a US localized device but want to additionally purchase EU mapping. To update your OEM map you'd normally use GarminExpress, when you purchase the map you get the option to add it directly to your device and/or load it you your PC so you can select tiles like in the image shown in Post #92. Unfortinately GarminExpress connects with devices only in Mass Storage Mode and your SP cannot do that so you need to use MapUpdater which is old and may not even work properly now:
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Garmin regards all streetpilots as obsolete/end-of-life so you'll get no help from them. The warning on the map store is 'generic' for SPs, however only some SPs cannot use NT mapping, SP26x0 for instance. Certainly SP2720 can use them. I have a US 2720 with Lifetime Maps subscription, I can still update it easily from the PC Data on my computer.

OSM mapping is quite good and I use it in a SP2620 which isn't NT capable. Certainly SP2720 can use OSM data without problems. I'd not say that OSM is superior to Garmin's NT City Navigators however but it does depend on the area you're operating in and in some cases OSM is at least equal for everyday use.