What is his biggest obstacle when it comes to convincing conventional ag farmers to switch to more 'unconventional' eco-practices as he is doing?
Very short answer from Gabe: "The farm program" he called it "antagonistic" towards what he sees as progress and good practices.
I can try to expand on what I think he meant by this knowing that Gabe doesn't use the federal crop insurance program or other USDA aid. For one, crop insurance places restrictions on the use of cover crops so that inter-seeding is, to the best of my knowledge, prohibited. There are many additional restrictions too, some depending on geographical region. Also any type of subsidy undermines the function of the market and potentially discourages farmers from taking advantage of free natural services to enhance soil health.
When I asked Gabe what he believes is his own personal greatest strength as a farmer he responded that it was that he didn't grow up on a farm and therefore is much more open-minded than the typical farmer. (My own thoughts starting here) Again back to the corn/soybean-centric farm bill, it does nothing to help shift the paradigm and look for a better model.
On a side note, I've found a silver-lining to the farm bill thanks to the hard work of a few individuals who I believe include Mark Shepard. The conservation stewardship program includes funding for activities that read like they were written by a permaculturist and I'll be using this funding to establish an acre of edible woody perennials in 2016, there will be a thread on this!