I live near Toronto, where they hold a big tournament every year... so despite Canada's lack of top players, there is still opportunity to see the best of the best every year. And, if you want to take the trip to Montreal, you can see both the men and the women in the same year. NYC isn't that far away either...
I don't remember exactly what made me think "tennis is great!". I recall watchig Wimbledon at my fathers when I was young, because my step mother has been going to the Toronto tournament since she was a wee tot.
I also recall watching Wimbledon at my friends house a few times... she liked Pete, I didn't
The first year i went to a tournament was 1999 - the Canadian Open finals with Hingis and Seles.. I was a Hingis fan. I think that trip was my idea, but I'm not entirely sure.
I didn't start following tennis on the internet until after watching Marat Safin in the USO 2000.
I didn't answer your question at all, did I?