I just bought the BlackHat Auto Responder (BHAR) at blackhatautoresponder.com. The only problem I have had with it is trying to view the tutorial about how to set it up. It has no sound which bothers me a bunch. I have a Mac too.
If you can't afford anything you can use thunderbird (free from mozilla is based on open source outlook) and you can use the vacation settings with a delay on the refresh and even get a timed auto responder (example set it to check for mail every 3 hours, then when it checks it will autorespond with the message you set as your vacation message) users mailing you get a naturally looking, because of the delay on check, auto response.
When I had almost no budget and was into craigslist 3-4 years ago I used it and did a ton of auto responses through just regular hotmail and yahoo accounts and made a pretty penny Works fine IMO if you can't afford something sweet.
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