I also encountered Mapsource crashes on a route I was planning last week. No matter what I did, it crashed.
Ended up using the HD Ride Planner and it appeared to load ok on my 660.
Will probably invest in Streets & Trips. Appears they are phasing out Mapsource & Basecamp sucks hind teat.
From my past experience with Garmin, they do not give a zchit about HD Garmin users, and HD customer service agreed with me when I contacted them to eventually resolve my issue (not related to the above - my past issue was hardware).
Still using an antiquated (by modern standards) a Garmin 478
Upgrading maps is a real PITA. And if you don't keep the exact version on both the GPS and Mapsource, you get route errors, to the point any route you load will not route on streets, only straight lines between way points.
Still using Streets & Trips to figure where I am going first, but that is a 2005 version that will not load to the Garmin.
Don't like any of the S&T versions from 06 on so never upgrade that program.
It should not be this difficult.