I'll second the Learned Helplessness - your strategy currently seems to revolve around changing your parents, changing your immediate family and changing your town in order to stablize your life. Unfortunately, though other people can change, they can rarely (if ever) be changed by others. You need to stop focusing on the townspeople, the parents and the family, and start focusing on the thing you can change - your circumstance-strategy and your goals.
Here are a few things to consider, and some hard questions:
#5 - Why are you drowning in guilt, what have you done to feel guilty about? Your business failing? Your inability to support others who are not supporting themselves? Is your guilt misplaced, should you really be feeling responsibility?
I ask because guilt has a downward affect, responsibility upward - if you feel guilty that you can't support your family, you continue to sink into depression as you continue to fail. If you feel responsible for supporting your family, you find yourself needing to do just that and rising to goals that will fulfill that responsibility.
In regards to #2, I would consider this a cop-out. If there are no leaders, then you lead. If there are no innovators, then you innovate. If people want 9-5 jobs, then hire them, don't co-found with them. I realize that being in an "active" area can help in networking and support, but it also comes with disadvantages - competition for those same resources, false prophets and snake-oil salesmen, superstition-based strategy "Only 21 year olds can innovate, you need a 21 year old!", and it's own built in (false) positive-feedback loop. In my experience, "safe" or "inactive" areas are also usually somewhat economically depressed or limited - they rely on a factory or a set of services (hospitals, trucking depots) to supply most of the jobs. This can be a golden opportunity for an entrepreneur: there are probably lots of people there that need jobs or are working dead-end or low-wage jobs that would love a new business to open up in their neighborhood.
#4 Time to break the chain. If your whole family suffers from social-anxiety, it's time to ease them in to some new relationships. People need friends, and families need anchors. You can't do something creative or risky when you're floating anchorless. Your family needs to join the community, even if they do it awkwardly or slowly. My suggestion is this: choose an activity, sport, hobby or interest that at least 3 of your family share. I'm talking things like hiking, climbing, reading books, video games, sailing, motorboating, motorcyling, bicycling ... whatever it is that a few of you like to do. Find a local club that's related and join it. If there isn't one, start it. In fact, that may help you get your business chops back - running a small community club. Either way, you need to get your family "out there" and slowly the relationships will start to build. Once they have a few friends, they'll feel anchored to their community, their lives won't feel so out of balance, and taking risks will not seem so dangerous.
#3 I've never been faced with this situation so I'm not sure I can respond well. I'm tempted to say that if they don't want your help or won't admit they need it, perhaps you should let them make their own choices and back off.
Finally #1 - have you considered bankruptcy? If you're being smashed by crushing debt, the contracts you signed with those lenders hold escape clauses for you and them. Perhaps it is time to exercise yours?