Smoghat, it sounds like you've been peripherally involved with art in some respects for some time. I'd be interested to know more about your artwork, your professional field and how it relates to art - feel free to PM! It's been said there are no art worlds, there are art villages. In what village does the work you make fit? What form does it take? What's your intended audience? I take it you're not interested in painting for calendars (nothing wrong with that) but perhaps something more intellectually engaging.
I won't be retiring to art, but am using MMM as incentive for frugal habits that will keep my art practice sustainable over the long term. I have a BFA in painting but it took me many years to warm up to contemporary art. Historic processes and imagery had much more interest and still hold some for me. In the meantime, much of what I did art-wise was not relevant to society today. Now? More so, but I'm still on the emerging end of the scale at 43. This is also because I left the US 15 years ago for Asia and have moved around too much to be part of an art community. I'm immigrating to Hong Kong (where I've lived or visited for a decade), and am finally settling in for the long haul. Previously I had a sole proprietorship here but will probably set up an LLC this time around, since some of my projects will involve import-export and possibly liability in terms of materials used. Would be interested to know more about how it's been challenging for you to accept art payments via an LLC.
An artist-in-residence gig on renewable 2-year contracts got me here this time round (via Beijing), providing the income and stability and time for other projects. I've done a number of residencies in places including Malaysia, Tibetan Sichuan, and soon Barcelona. Ran an informal one at my flat in Sicily for a couple years. It's useful to look at what your goals are for a residency to help you select the right one(s) for you. For years I looked at opportunities via mailing lists like Residency Unlimited, Resartis, Art Opportunities.org. Not sure if this answers your questions at all but in order to give useful advice would be good to start by seeing your work!