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Sign up for a pay per click service and check every single one of your domains. Then let the bottom line decide if your name is worth holding or not. If you don't want to sign up, then I can let you point it to my account and I will give you the stats. Basically, if one of my names generate revenue > 125% of the annual reg fee, then I keep it. In most cases, you need to watch a name for at least a month to know what its potential is. Although my focus is on domains for resale, getting some steady income from traffic domains is just fine. Around 5% of my portfolio are typos which I keep just for the revenue.
I'll give you $1 for the domain, and see how it does on typins for the next month. If I decide to renew it, you can have your choice of $10 or half the profits from the domain for as long as I keep it. (I'll show you the stats)
Well, everyone's been saying drop... If he drops it, he makes $0. If he sells it to me, he could make $1 or $11.
Pick a price and offer Chiccago.com in domains for sale. If you can do something like offer a free/low-cost trial or money-back guarantee (since you can't show any typin statistics), it will sell easily. That's what I'm getting at.
This may not work with domains totally flawlessly- it's just that I've sold so many things using free trials and money-back guarantees that I'm kind of biased.