My opinion on this thread:

The DB is not a huge upgrade framewise over the Masi and it has old 10 speed 105.

I got 10 speed 105 from Ribble for about $400 a couple of months ago. You still may be able to find a group on Ribble or Merlin for that cost. 11 speed is not much more expensive and more readily available but then you need new wheels which is probably $500 for 11 speed wheels at which point you might as well buy a new bike.

That Motobecane is one of the ugliest frames I've ever seen

I bought a new bike that had a standard crankset and yes it made a noticeable difference on my rides that involve a lot of climbing and it's mostly Cat 3 & 4. I immediately bought a compact crankset to replace it and I've been much happier. But you are not me so maybe you are much stronger. The 105 group I bought for my second bike is standard crank with 12-27 cassette and I'm able to get up the same hills with it but when it comes to 30-40 mile rides with lots of climbs I leave that bike at home