The 14 day claim period is a huge stumbling block. The last thing I would want to have happen is not being able to get the funds back in the even that the person was somehow *not* able to claim the funds. Basically this puts the risk exposure to me somewhere around the $20 mark for using that service.

For example, I just made an auction purchase for $785, there is no way I would ever send that via a service that could claim the coins after 14 days if for some reason the recipient didn't receive the e-mail, etc.

The site (that I'm proposing) really needs to define itself as the payment escrow/caretaker for those that don't have the knowledge/resources to conduct the transaction directly with the current Bitcoin clients. Piggybacking on a current exchange/online wallet service that can ACH transfer funds directly to a bank account would obviously be of great use as well and rapidly spur adoption. Essentially it's all the familiarity of using a site like Paypal, except instead of $ it's BTC.

How you would monetize the service to pay for hosting, etc - I'm not 100% positive. However the startup cost for developing/hosting such a thing is so nominal these days that I would rather focus on something that services the community first, figures out how to build a business around it later.

Again - if someone is serious about attacking this - I'm happy to discuss in more detail.