That's a good question. After thinking about it for however long it took me to read the replies to this topic, I've come to a conclusion:
Probably. XD; I think it would be a lot of fun, but I don't know if it would work in our world. We're so industrialized and, unlike in the "Pokemon world", the cities and towns are so spread out here. =\ I mean, I'm thinking that all the different countries in Pokemon are around the size of Japan, which is big, but if I were to go on a Pokemon journey starting from my home, in North America... it would be a big job travelling to large cities where the Pokemon gyms would be situated. :x If I started from Kanto or something though, I would be fine, I'm sure. I just don't like walking long distances because I'm lazy. XD
I'd love to work with Pokemon, though. Like Orange, I bet I would end up being a Pokemon Watcher. =\ Being the typical trainer would be pretty boring for me... I'd much rather be able to stop and draw Pokemon whenever I wanted since I like sketching animals really quickly too. ^_^; I'd probably travel alone, since I don't usually like people near me 24/7, but I guess it might be fun to hang around with a trainer or something. Not another watcher, though. =o I'd either get jealous of their drawings or I'd have to humble myself too much if they sucked~ XD