I tested the sell v. donate approach so many times. How could I possibly donate a pair of Coach sneakers that I let my daughter convince me to buy for her and she only to wore once or twice? Here is how: by using "Itsdeductible" valuation tool (online) and eBay as a means of determining market value of the pricier items, I lowered my overall tax position so much that I didn't have to pay any income taxes for three years and counting. When you think of all the time you spend setting up an ONLINE AUCTION SITE (i.e. eBay) ad, communicating with potential buyers, packaging, shipping, etc. etc. you can "make" almost as much by donating the item. Here is how: Say you sell something on an eBay site that cost you $5.00 for $19.99 (with Free Shipping to attract buyers). By the time you pay eBay fees $2.35, shipping $6.00 (or more), PayPal fees $1.00 (est), packing materials $1.00 (or more) and gas (if you drive to the post office), time leaving feedback, following up on payments or (worse) handling disputes....you have made a profit of approximately $4.00 for at least one to two hours of your time. If, however, you can find where a similar item sold on eBay for $40.00 (very easy to find) and your tax bracket is 20%, then you can donate that item and have approximately $8.00 less of tax liability... $3.00 "net" profit after original cost of $5.00 for item... for approximately 20 mins of your time v. 1 - 2 hours it takes to sell the item on eBay, Craigslist, etc. If you donate enough items, you may even lower your overall tax bracket a few more points.... saving you even more in taxes and, possibly, allowing you to qualify for tax credits you may not have qualified for had you not donated so many items. There is a limit to how much of your gross income can be lowered using donations, but it is generous (consult with your tax program/professional for more detail). I am NOT an accountant or a replacement for professional advice: I just know what has worked for me for several years running. I have gone so far as to pick up items from yard sales just to donate them because I know the value of the item. (i.e. chrome shower curtain hooks: $1.00 at yard sale, $20.00 value on ebay, $4.00 less tax liablity = $3.00 more in my pocket. I have gotten so efficient at this method, that I have gotten my start to finish processing time down to 5 - 8 minutes per item v. 1 - 2 hours of eBay and/or Craigslist selling. Craigslist selling is also time consuming and very risky business...even if you try to limit the buyers access to your garage. Even the tools in your garage can speak to a thief's assessment of what might be in your house, where your doors are, if you garage has a back door... As with all tax matters, keep good records: Take pictures of all items being donated (1 picture per item is fine as long as the quality of the item is good or better and captured in the picture and charitable organization and their receipts meet IRS guidelines. IRS guidelines pertaining to language on receipts is very stringent!! Be careful there.) Plus, by donating, you are helping others so it is a win/win 🙂