How is Alan having so much trouble with money? I mean, he's no longer paying alimony to Judith, or Kandi(I believe) and Jake is now legally an adult so he doesn't have to pay child support anymore. How can he be broke? I mean he was able to support a wife and a kid as a chiropractor, so how come now he can't support even himself? I even wonder if he still has a job. Poor writing, I'd say.
If he's not doing well as a chiropractor, then perhaps it's time he looks for a new job/career. Maybe Walden should give him a job at his company.