First things first: in the title you will find "northern" italy. Our area is more what people imagine when they think of germany. Certainly not what passes for most hollywood visions of Italy. It's nice, but it's not Tuscany or Sicily, especially in the winter which feels more like England.
Climate aside, I feel that I'm sitting on two potentially awesome opportunities for someone who wants to dedicate themselves to something promising with a minimal economic investment. Probably the biggest investment would be your time.
There is a big generational flip happening here and lots of great things are around with nobody to tend to them. The children are perusing modern careers and their aging parents are sitting on a patrimony in terms of genetics and market-access. What is even better is that (at least from my vantage point) there is the willingness of the older generation to support projects leading toward sustainability/regeneration.
I'm purposely going to be vague in what follows. If people are interested, they can PM me for more details.
One project would be taking over a tree nursery. Knowledge of italian is important for this one.
Another project would be designing a small-scale (2 acres) project based around one niche market product. This would have the backing of a economically solid commercial entity.
For both of these projects, and especially for the second, I would be taking an active part, so anyone looking to "land softly" I could help out with getting them situated and designing the whole "getting started" aspect.
I don't see this as being along the lines of a wwoofing experience, since the commitment is pretty much long term and it's designed to lead to a economically sustainable business. However, if there is someone out there with a lot of time and a little money but no land or project to take the lead on, this could be a great opportunity.
As long as you want to live and work in italy.
And now for the big let-down (at least for non-euros): staying in italy legally for the long-term is not impossible, but nearly.