So, I was wondering if this is a game that I could be successful at playing. I've played a few other simulation racers before; most notably Forza 3 and NFS: Shift. I love the feeling of being able to successfully get my car around a track without humping a wall for half the race. 
 
I was able to start to turn off a lot of the assists in Forza 3 but NFS: Shift really frustrated me. In both games I was never able drive with manual transmission (I've only ever done that in real life with a motorcycle) as it felt very awkward. I'm sure if I had spent more time with Forza 3, I might have been able to work my way up to manual transmission. 
 
Now the question is: Is this game approachable or am I going to spend countless hours humping a wall and feeling unmanly for poor driving? Is it possible to learn how to race with a stick in this game? Would I be better off just looking at pretty pictures of cars on the web?

...the assists in GT5 are a joke.  All you need to do is gas and break when it tells you to, and slightly turn.  I turned them off after I realized what was going on. 
 
Plus, the Licenses are supposed to teach you how to drive, so it's best to try to do them with the assists off.   
 
Special Events are pretty strict with getting golds too, so you might be able to pick up a thing or to. 
 
Just play the game offline.  x.x

I think the key to success in learning how to drive with a manual tranmission is to set it that way by default before you even start your first race. Also, you may want to remap the controls so that L2 and R2 are your brake and accelerator and X and ❒ are your shift down and up buttons. It helped me. 
 
The game does a good job of starting you off slow and then easing you into more difficult races and more powerful cars. I think you'll have fun with it if you have the patience to deal with the shitty UI and ridiculously long load times.