What is the best way to go about contacting people from that industry and trying to sell them the domain and site? I have portland-personal-trainer on page one of google #1 position in yahoo and page 2 of bing... any ideas?
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Do some searches for your keywords as you have been doing, then look at some of the sites and paid ads. Make a list and then contact the ones that don't seem to have very good domains. Try them first and then try the ones that have pretty good domains because they may be interested if the price is not too high. If they can buy a domain and get more visitors, they may be able to same money on paid ads.
The hard part will be to set a value on your domain that gets you a good price, but is not so high that no one wants to buy it...
Good Luck!