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Assuming you already have specified where you wish to go, and the device shows the map (of your current location) on the screen,
you can touch the screen to see the MENU screen ... then look for (on the Menu screen) a browse map option, and you'll see the route (to your destination) displayed.
If you're looking for a list of turn by turn text instructions, e.g. turn right to XXXX street, go for NN miles, etc. you may not find it displayed on your TomTom device.
There are settings in the GPS that allow you to pick what type of routes you want to have the unit pick for you. They can be based on time, distance, or least fuel used. You can also do the following: if you know at least part of the route to your destination, and the GPS doesn't pick the particular way you prefer you can just start driving off route. The GPS will realize that you are off route and it will recalculate itself. You can also add "Way Points" to your route that would force the GPS to calculate the route to the way you want it to go.
The error during planning is a map error not an OS error. It will give you this warning if you try to nav somewhere that it cant see any way of getting to because there is a gap somewhere en-route. Normally its the last 100 yards or something. The workaround is to nav to an adjoining road or somewhere very close to where you want to end up. Oddly or maybe coincidentally (which I doubt at 60,000 miles per year) I have only had this happen on the new maps.
In general, once you key in an address and then select a route, the name/route will be saved in "recent destinations." If you want to use that destination, just select it. If you want to add it to "Favorites", then select "Add Favorite" and all your recent destinations will appear. Select the one you want and rename it: E.g., instead of "220 W. Walnut St." rename it "Grandma's House" and it is set.