OK I admit it. I am an online contest whore (or addict - pick your favourite metaphor). My first positive online contest experience - I won an autographed Clapton/B.B. King guitar in a promotion for their "Riding with the King" album (details here). Eventually I sold the guitar -- the sale sponsored a trip for Pat and I to California to a race in Laguna Seca in 2001 (where I met a very young Patrick Scoble with his father), purchased an Ernie Ball guitar for Matt and I am not sure what for Catherine.
Since then I have entered many online contests and won a few - mostly Blue Jays and other tickets, occasional product sample packages -- once a $500 certificate for shoe purchase and most recently a trip to Paris for the launch of the Gregory Charles album.
A few tips:
- I find contests at contest sites and every where I go -- I am on the net a lot.
- I supply a throwaway email address just in case there is some leakage to spammers (though I have yet to experience such a leakage as far as I know)
- I rarely enter contests that require pin numbers, UPC codes, submission of photos, videos or essays -- just too much trouble