I always play characters I enjoy playing, but there's definitely something to be said about playing a good character.
I've been debating making a post on 9/25 with my tier list, but I don't know yet. I figure someone is going to make that post no matter what, so it may be better if I start things off since I'll have more knowledge than most everyone else at that point. But I don't know if I even want to bother with tier list discussions... they never end well.
Whether or not you make one, as you said, it WILL be made. You're just one of the few people who will actually breakdown each character to figure out their place. I'd be willing to take yours as one thats at the very least thought out. So, personally, I think you should, and not just because I'm a "tier-whore." I mean, regardless my character will probably be between Tina, Lei Fang, and Jann Lee, unless they are all garbage tier.
qoodname, being serious, when I train anyone at a fighting game, I tell them to start off with a high tier character just so they can learn the game at the easiest level first. I learned the game on Kasumi, I got wins, but she wasn't for me, but she taught me the game well. I'm teaching a guy to play Street Fighter and he wanted to play Gen. Gen is NOT a beginner character, so I gave him a list of a couple characters to choose from to learn the game on (Boxer, Dictator, Ryu, Honda). He chose Boxer. At my first RanBat his Gen got absolutely bodied. At my second one two weeks later his Boxer got 4th place.