Bob hasn't updated his computer to Windows 10 yet because he uses an app called Microsoft Map Point, which won't work with the updated OS. What Leo recommends is to go ahead and upgrade to Windows 10 to get the upgrade, and then roll back to Windows 7. That way, you can still have the upgrade entitlement when you're ready to move forward. But you can also look at other map apps. There's plenty of alternatives out there, like Google Maps and Waze. Bing Maps may also have similar features, and there's also Windows Maps, an app in Windows 10. So take a look at that.
From the Chatroom, although it's not officially supported, there is a way to install Map Point with Windows 10. Check it out here.
Jim in LA called at the end of hour 2 to add that the AAA website still offers "Triptiks," a travel planner where you can create your own maps online with multiple locations and then download them