Well farm lands are not a problem with me since a good part of my regular rides go through some pretty pungent areas.
But the wind factor is a good point. Of course that assumes there will be wind on the days of our ride while in other areas the mountains will always be there.
We already have plans to incorporate trains into our trip. Perhaps to get us over the rougher sections.
I'm thinking maybe SE from Milan to Parma then a train or bus from Parma to La Spezia. The hills along the coast South of La Spezia don't look too bad besides it seems to flatten out pretty quickly.