So, I'm starting to place more things on Craigslist and Ebay. I've been loathe to do this because it's really a pain in the butt just to list things. Plus, on Craiglist you (or at least I) seem to get a disproportionate amount of responses saying they'll come buy something and then never show. (What's with that?)
I'm starting to get a bit of a good system down, but would readily welcome more advice. For anyone else who hasn't even gotten this far, here's what's working for me: First, and foremost, an internet-connected camera. This can be as simple as a phone with a camera and a data plan (or at least Wi-Fi). I take pictures with my phone (which is currently a MyTouch 3G (Android)) and have an application running that automatically uploads the picture to multiple web locations. I've also had this setup on a Windows Mobile phone before, and I know it's possible with an iPhone and Blackberry, so the gamut is mostly covered. Here are some great contenders:
Shozu:I was using Shozu on Windows Mobile before, and immediately went to get it for Android when I switched over, but they currently don't have an application for this OS. I liked it a lot, but in hindsight the setup is not quite as intuitive as the solution I wound up with. However it's good, and reliable.
PixelPipe: Google quickly brought up PixelPipe when I started seeking out alternatives, and I went so far as to shell out the big two dollars for their pro version of the Android app they offer. In my opinion the only thing this one is lacking is the option for automatic posting, and this is the primary reason, to me, to use any application like this. I want to just snap the picture and have it immediately placed online. Too bad, because it seems that you can access PixelPipe via far more methods (i.e. Mobile, IM, Picasa, Ubuntu programs, etc.) than any other media-publishing app. (also note the primary difference between their free and pro apps is that with Pro you can upload video.)
I wound up with ITookThisOnMyPhone and think it's absolutely the best. Not only is it free (though I'd readily pay for it), but it has the automatic uploading of photos that I so desire. It works consistently, and you can set up privacy-based rules for photo publishing, which is an added bonus. I currently am mostly pushing my photos to PicasaWeb, which I can then from there either download locally or push to Facebook as I choose. But the labor of getting them off my phone is DONE for me.
So now that I've got the photos of the items to be sold online, I search around for similar items to get a feel of the item's appropriate description and price (sometimes straight-up copying and pasting with a little tweaking, ahem) and then start describing my item. I use (used) the Firefox plugin "DragDropUpload" which lets you just drop a file from Windows Explorer onto a file upload dialog box - so you never have to click "Browse". As I write this, it's not compatible with Firefox 3.5 but hopefully that will change soon.
Before I submit the posting, I add some easy contact methods for people that still keep my anonymity: Meebo and Google Voice. The latter is still not quite open to everyone but that'll change soon, too. By "adding" I mean that I've set up individual HTML pages that contain the widgets provided by these tools. This way someone can instantly IM me via Meebo, or call me via Google Voice.
Finally, I've set up some filters in Gmail so that anything referring to my Craigslist/Ebay sales will be automatically flagged with a "sales" tag, so that I can keep things organized in my usually-overflowing inbox.
It's working fairly nicely.
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