We investigate some of the most infamous stock market superstitions with Morgan Housel and taste test the best goodies pumpkin spice season has to offer. It’s a very Halloween episode of Motley Fool Answers and [spoiler] it’s going to get weird.

Should you pay down your mortgage or invest the money? Are annuities good or bad? Collect Social Security ASAP or wait? We debate the merits of both sides of common money conundrums. Also, we head to the mailbag for your questions on managing your 401k yourself, owning your company’s stock, if it’s ever too late to open a Roth, and more.

We found the diary of a financial advisor and brought him on the show to talk about the surprising things he’s learned throughout his career. Also, is being frugal in your DNA and can a family of four really live off of $14K a year?

Mailbag time! James Early is back to answer your burning questions about swanky-sounding preferred stocks, the pains of loving MLPs and how to convert your portfolio to a dividend producing machine.