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Chris,
I've used ebay a fair amount and made some large purchases and sold a couple of expensive items. I have never had a serious problem, but when buying anything of significant value I always check ebay feedback, google for info on the seller and bounce a few questions off them to see if they are responsive and knowledgeable about the item they are selling. A couple of times I have decided against buying an item I really wanted because the seller seemed a bit flaky.
When selling I always take pictures of the item pre and post packing and send the item via registered post or a courier who provides proof of delivery. I'm also scrupulous with my item descriptions, so a buyer shouldn't get any surprises.
Despite all reasonable precautions I'm sure you can still get screwed. I figure the occasional bad transaction is balanced by all the good ones...
A general tip on buying strategy is that sniping at the last minute will usually save you money. I just use a tabbed browser with a bid ready to go in one tab while I watch the countdown in another tab. Don't get caught up in the excitement and bid more than you planned to spend, of course.
For selling, if you have an item that is likely to be popular then set a very low starting price. You'll attract a bunch of people hoping for a bargain and take advantage of what behavioural economists call the "winner's curse".
Cheers,
Rick.
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