...if only they had worked hard and put away a few dollars in their 20's, they would be much more free now to pursue their art.
If they'd worked hard at being artists and put away a few dollars in their 20s, they would be artists now. If they worked hard at being accountants and put away a few dollars in their 20s, they would've found excellence and stability in that field, and not pine for life as artists. It sounds like your musician friends have a lack of work-ethic combined with a regrettable overabundance of talent. I've seen this many, many times.
Professional artists support themselves through their art, and make choices that help them do that; anyone else is a hobbyist... and that's great, people should be well-rounded! However, an accountant who wants to be a nurse doesn't tell her tax clients, "I'm really a nurse. This is just my day job." In the same way, there is no such thing as an actor who has a day job as a barista. There's just a barista who wants to be an actor, but isn't one... yet.
I've been a successful, professional performing artist since I got out of college, working with other successful, professional artists of both the performing and visual variety. I've never known anyone with a trust fund, just people with talent coming out their ears who work like dogs. Most of us are married to other successful, professional artists. Most of us own our homes. Most of us have children and pets. We keep within our own social circle, since we come up against amazing assumptions and prejudice from civilians who think what we do is frivolous, easy, and overpaid, and that we're all pro-union Democrat atheists. (The stories I have from my own family and first dates would make your hair curl.)
The people in my company--which offers an FSA and a 403b--range from lower-middle class to multimillionaires. We have health insurance and pensions through our unions. Some of us middle-class types will have great retirements, and some of us multimillionaires will be impoverished a year after we stop working... just like people in "normal" industries.
That's really my point: artists have the same foibles as the general population. Many lack drive and/or financial sense. For people whose job it is to be creative, some artists are amazingly unwilling to think outside the box. They're often
more resistant to diversifying their primary asset--their career--than civilians.
While artists have the same foibles at the same percentage as "normal" folk, there's no room for normal folk to be professional artists, there's only room for those with the most talent. Not only that, there's only room for the most talented WITH cutthroat ambition. Successful artists attend auditions and interviews,
and also look for a back-door way to land a gig (any other job in the building even if it's as a security guard), go over their address book looking for a connection, and scheme ways to get themselves into a social situation with the people in power. They sell their cars, go without cable, and sleep on a friend's couch for three months to save the rent in order to do the low paying gigs that will further their careers. Being a professional artist is not an impossible, impracticable dream, but you have to be willing to do what it takes, and most people just aren't willing.
Universities pay me to give advice on "how to make it in the arts". Know what it is? Work hard and be a good person.
To freznow: the time to pursue circus arts is always NOW; athletic endeavors are for the young. A for-profit like Blue Man or Cirque probably has a 401k; be sure you're in a position to take advantage. Watch your pennies, and save up for the transition all dancers/acrobats make in their 40s. Why, you can't throw a rock without hitting a "Career Transition for Dancers" seminar through Actors' Equity or AGMA.
