"Enterprise" Java does not need to be the way you have experienced it. We are getting ready to release a fairly complex Java application that addresses a very significant pain point. The major components of the entire application are highly decoupled. Our team is currently two developers, and we do not envision it to grow over three. The whole development process took only 8 months.
So... don't blame Java for poor architects or poor engineering/business leadership...
(And, btw, I'd love to talk to you if you are in the Boston area.)
I'm not sure a catastrophic collapse will happen any time soon (unless as a byproduct of some non-financial catastrophic event - e.g. a meteor hitting NYC). Since currency values are only relative to each other, any loss of value of the USD has to be matched by a strengthening of other currencies. The Euro is in no fighting shape, and an eccessive strengthening of the Renminbi would have catastrophic domestic effects in China (hence the Chinese government would simply not allow that to happen).
But... let's say you live in the US and want to prepare for it anyway? The major effect would be rampant inflation, especially for goods and services that are either imported or are highly reliant on imported goods. We import very little food (although we rely on oil-based fertilizers to make it), so I do not believe that widespread chaos and street violence ("kill your lunch, chop your wood, and carry a gun" scenario) are very likely.
To protect yourself from inflation, don't focus so much on your financial assets as on your personal and professional assets. A financial bet can go wrong (what if the USD strengthens instead?), while your skills and ability to generate income will always benefit you. Develop a freelancing business and related skills - salaries adjust slowly to inflation, so you get squeezed, while as a freelancer you can adjust your rates more quickly. Also develop a lifestyle that relies as little as possible on our major imported commodity, oil - a fuel efficient car, solar panels on the roof, etc.
Back in 2000 I did a startup with a B2B web-based app for an enterprise vertical (large homebuilders). We tried both hiring an enterprise sales guy and schlepping it ourselves, and here are my take-aways from that experience.
"Successful enterprise salesperson happy to join a cash strapped startup" is an oxymoron in more than one way. Other posters explained it: these salespeople expect big support, big budgets, ads to generate leads, junior staffers to screen the leads, etc. They also expect a lot of cash compensation: virtually all such people I have ever met usually like flashy and expensive lifestyles, because in what they do the appearance of success is one of the factors that breeds success. I remember one guy who seemed very enthusiastic about joining us, but then the deal fell apart because in his contract he absolutely would not budge from first class air travel and Jaguar-class rental cars.
Then we decided to do it ourselves (the founders). We networked the hell out of any friend we had, and our intro to prospects was "Look, we are not sales guys, we are entrepreneurs. We think we have a kick-ass product and we'd love to show it to you, and since we are still small the price to you will be super-cheap compared to the competition if you help us improve it to fit your needs." That way we eliminated a lot of issues and we tried to compete on a different playing field.
The result: we got clients to work with us, and the sales guy we hired never managed to go past a first meeting.
I've used iPrint several times. Once they completely screwed up the order (I received somebody else's cards) and once the quality was so-so, but in both cases they were very good at making it right. Overall I'd use them again.
I have one piece of advice for you. Make sure that some of your early failures include other people. Many issues that bring down startups at their core are about people, not technology.
So... don't blame Java for poor architects or poor engineering/business leadership...
(And, btw, I'd love to talk to you if you are in the Boston area.)