I can understand your points, the situation both bureaucratic and the doubts to be a farmer are quite similar here in Catalonia and in Spain. I guess it's a sort of a Southern European particular dilemma.
First of all, I think it's true what you said that by cultivating and selling vegetables, even with the organic certification, it's very difficult that you can barely make a living. The few people that are having some success over here with this approach are the ones who prepare and sell weekly baskets of fresh veggies to certain interested people. The key is obviously to find that handful and loyal group of local people willing to pay in a regular basis, so this kind of initiatives use to come not from scratch but from previously well-established initiatives. I think in the US the weekly basket and similar assured buying approach is called CSA (Community Supported Agriculture).
About the crowdfunding stuff; I've been actually a crowdfunder of a local olive oil producing cooperative. They basically have 0 money and lots of Hectares of olives, so they do the crowdfunding to get the money before the harvest, and after getting the oil they give it to the crowdfounders and sold the rest at local CSAs. To implicate the people to attend and get in touch, they invited them to help them catch the olives, so it has also this kind of community-building spirit, which is attractive for many of us. So, according to my experience, crowdfunding may be a viable way for some punctual and particular projects like the olive oil harvest (we Mediterraneans have a special crush with it, isn't it?) or other similar seasonal jobs, but less so with entire (permie or not) projects, which would require a much more personal involvement other than paying money and receiving an item in exchange, that is what we are most used to.
I have no land of mine but I've been thinking along similar lines than yours, and I've reached the conclusion that until economic and resource circumstances change for the good, food-prepared stuff is the best way to get a bit of a profit from land products. For example, instead of selling tomatoes in the market, which thousands of "industrial" producers sell it in a much more reliable regularity and low price than you can do, you could learn to prepare and sell "home-made local organic tomato jelly" in a CSA scheme or even in a more open local market. Another example that comes to mind would be instead of selling the chickpeas directly (well, you're probably going to get a lot, so you can do a 50-50% approach to try which is the most profitable way) sell already prepared "home-made local organic Hummus".
Anyway, don't get yourself too stressed, and as you said, try to go one step at a time. (yes, easier said than done, specially with that loan in mind, but having another couple of jobs to rely one for a stable income is quite encouraging). If I had a piece of land of mine to practice permaculture, I'd follow something like a three-year plan, in which I'd spend the first year experimenting, trying to grow as many varied food as possible to see how much can I lower my family reliance on external (i.e., money) food supplies. Once done, I would go the second year into learning all kind of permaculture tricks, like ways to process food (jelly making, recipes, etc), arts and crafts, etc, and sharing this to my local people so they start knowing how good I am in getting that jelly done, while I would also be lowering my food and stuff dependence even more deeply. And finally, in the third year, I'd be confident enough to start telling the government that I want to be a farmer (you know what I mean), so I could begin selling my produce and create or co-join with other similar people a local CSA scheme. Well, I'm a slow-learner and this timing could be definitely reduced depending on one's preexisting skills, and necessities, but it was just an example so I could give you my two-cents on the issue.
So really hope you can have much luck with your project, and just tell us about how's going.
