Recording the aftershows is a great idea. The couple of times I've stuck around, they've been interesting and fun so sign me up.

Print-on-demand services are kinda expensive, but it doesn't cost you anything and there's no risk, you can experiment and figure out what works. I'd totally recommend Zazzle, they have done a great job for me in the past.

The nice thing is, you can start offering products through print-on-demand right away and use the revenue and experience to pick up just what inventory you know you can sell in a realistic amount of time. Though the thought of you surrounded by giant piles of WPTavern tshirts does make me giggle ;)

Only a few more weeks until your hundredth episode, how exciting! Oh, and good luck with your house, next time send Chip...