Transaction advise for Craigslist purchase?
 

I was wondering if anyone had some advise on techniques on how to best handle a remote purchase transaction on a service like craigslist? Of course this could be applicable elsewhere, but craigslist is what I'm dealing with.
With eBay it's considered standard to purchase an item, make the payment in full, and have it shipped to you by the seller, I've done it plenty of times with very few snags. But an CL, where you don't have the self policing nature that eBay has, what would be a reasonable scenario in handling the sales transaction if not wanting to travel to other city/state? I've found a nice bike I'd like to purchase in the San Diego area while I'm in Portland OR. I've made contact with the seller, received confirmation pictures, discussed preliminary shipping options, but now the snag, he would like the money for the purchase up front prior to sending it.
From his point of view I can't blame him, but likewise, this puts me in a very sensitive position since obviously sending this large sum of money to someone I know nothing about is risky business.
Any experience from anyone working through this process?
thanks,
Karl

Maybe talk to the seller and see if you can find an escrow service that you can both agree to use. Make sure you find a reputable one, though. There are a lot of scams out there..

I've always dealt local with CL. I agree with you, this kind of stuff would be risky, no real way to ensure a mutual transaction.
My best recommendation, deal local

+1 the whole reason for craig's list was for local deals to get away from flea bay.

This can be done very easily with Paypal. The seller generates an invoice for the total price via Paypal. Paypal sends you an email saying the seller has requested payment. You logon to Paypal (go directly to Paypal, don't click on a link in the email). You pay the invoice via Paypal, but fund it with a credit card rather than bank transfer. This way if there's a problem, you can dispute it through your credit card company rather than Paypal (who charges a $25 fee for the seller to dispute something). In the notes to the seller section during payment, describe what you are buying. Include a link to the CL listing. This way there's a Paypal record of it.

When the seller receives payment, they box up the bike and ship it. For their own protection, the seller should include delivery confirmation, and maybe even signature required, on the shipping. If they fail to ship the item, it doesn't arrive, or is not as described, you can contact your credit card company to dispute the charge. If the seller cannot prove they shipped the item and that it arrived at your residence, they have no claim. If the bike isn't as described, you'll have to prove it to your CC company.

Under no circumstances would I send a personal check or money order to a stranger for such a sale.