I just tried to update the maps on my Zumo 660 that I've had for about 2 years and have updated numerous times with not problems. I started Garmin Map Updater 3.2.2, it found my 660, I agreed to the terms, it showed me the new version of the maps, I clicked continue, it said it was connecting to the server then a message popped up "This Garmin GPS is not eligible for this update because a previous map version is not installed." What the heck!!!!
That is strange ... did you get an option to enter a product code, I think it comes up on the first few pages but you need to look hard, if so select that and enter the product code that is available via myMaps on myGarmin.
Well I got the 2014.20 maps installed. I can't believe I did this but I installed Garmin Express ver 2.3.12 and it worked!!! I swore I'd never use GE after the last fiasco but I figured what the heck I'd give it shot. I'm not a convert yet, let's see if it works next time then we'll talk....