Research Pricing (And Set Fair Starting Prices): Before setting prices for each item, research your local Craigslist website and (if possible) nearby yard sales to get a sense of how to price them. Remember that many buyers will try to haggle – so set prices a bit higher than your bottom dollar, but not so high that you’ll scare off first bids. 10% to 15% is a good rule of thumb. Consider bunching low-value items, such as old CDs, into lots of five or 10, or offer x-for-$y deals.
I wasn’t thinking so much of plagiarism as I was about the simple act of someone sharing and passing it along to someone else. With e-Books, for instance, although I know there are several formats for them, I assume they are mostly PDFs to download. I don’t think it’s possible to password protect a PDF for opening (I think you can do it for printing or editing), nor to have some kind of time limit on being able to open it. As for courses, how do you ensure that the link or file doesn’t get passed around and accessed for free by people who didn’t pay?
Before you really roll up your sleeves and monetize your personal or professional skills, why not right-size your life? Selling your unwanted stuff is a great way to downsize and declutter your life while earning some income on the side. If you’re transitioning to full-time work-at-home status, that income could provide a critical boost to your plans for a proper home office, or allow you to maintain your lifestyle during lean times without resorting to voluntary simplicity.