I confess I have not read this thread from beginning to end, but here's my 2penceworth
An unstable/highly varied job record is probably more a symptom of ADHD than of Asperger's. My own job count runs into 3 figures.
In the late 1960s, I was lucky enough to acquire a skill which was in high demand by employment agencies. It was called Computer Operating, and it has long since ceased to exist, but for a while, I survived by moving from contract to contract on a daily or weekly basis. This was interspersed with periods of employment as a conveyancing assistant in a solicitor's office, a farm worker/tractor driver/livestock feeder, and a canal boat driver. I also spent time following the hippy trail through Europe as far as Istanbul.
After a short period as a builder's labourer, I discovered a need for somebody to clean the chimneys of houses ranging from the meanest hovels of the poor and needy through to some of the grandest stately homes in the land. For more than 30 years, this became my core income, but it was very seasonal, and I needed to find other sources of income mainly during the summer months. This ranged from being a night manager of a 24 hour store to driving the sick and elderly in ambulances to and from their day care centres. I also used the time to pursue an interest in offshore sailing boats, and for several years I funded my hobby by qualifying as an offshore sailing instructor in the waters of northern Europe. After a failed attempt to become a driving instructor, I qualified to drive trucks (articulated lorries) and for more than a decade I survived on a mixture of chimney cleaning and agency work as a truck driver.
As a schoolboy, I had been regarded as gifted, and was expected to go through university before carving out for myself a successful professional career. If I had been 'diagnosed' as having ADHD/Asperger's etc then it is likely that I would have become one of life's failures. But in those days, Autism was unheard of.
In practice, I never became in any way dependent upon any kind of state assistance.
The downside is that I have scraped through life as a complete loner - I have never made a friend, and although I married and fathered 3 children, I now live alone, and struggle with a very complicated relationship with my wife and children.
But my grandkids are great!