I know it's hard to give hints on playstyle if you don't know how someone plays, so I'll try to describe what problems I have and see if someone can give me hints.
Okay? tl;dr at the end, because I know this forum is not one of many words.
Let's see... first off, I'm only around 1000-1300 PP. Some days I do okay and rise a bit above that, other days not so well.
One of my main problems, I guess, is dealing with jump-ins. Even if I try to counter with moves that seem like good anti air, a lot of the time I'll only trade hits and lose more life than the opponent. I mean things like the standing medium kick. Perhaps my timing is off? But here's the word: "timing".
When I read through stickies and threads on this forum I find tons of possible combos. The game's own challenge mode suggests a few itself. Like the cr.lp mp hp, or what was it? But these are 1 frame links. At 60 frames per second, that's a 50ms window to hit the button. F**** me. These one frame link-combos are casually mentioned like "Oh, did you know you could do this?" But no, I can't do it, and I believe 70-80% of the SF4-playing population can't either. At least I never see people do them online. So you can apparently link a lk from a Hazanshu, but however many times I've tried, I've never managed to do so in training mode. After 100 tries I should pull it off at least a few times by mere chance, right? So LL loop my ass.
One thing that always gets me is how some characters can chain their specials together so that it's hard to punish them. Sagat goes over me with a Tiger Knee, I try to sweep and he immediately comes back with a Tiger Uppercut, hitting me out of my sweep while taking no damage at all. He whiffed, shouldn't it be my turn to punish? Maybe there's a window where I could have hit him, maybe I took too long to do so, but it's still annoying. I could have waited out the uppercut and punished him afterwards, but there's always a chance of the opponent just doing something else, and blocking too much is like an invitation to put on more pressure.
It's similar with the Shoryuken uppercut: After I block a Tatsumaki or something else they'll either do an uppercut or try to throw. I think there's this option select where you duck and press throw, but if I do that and the opponent decides to uppercut, Chun will try to do a cr. lk, which she then gets hit out of by the Shoryuken with it's invincibility frames. Or am I wrong? I wish I could say I understand the throw-tech option select but honestly, even normal throws often elude me. Sometimes I'll try to throw the opponent, hit throw and instead he throws me. What the...? It's not a command throw they'll do, and I've also had times when my character started her throw animation first and then she got thrown instead. Don't even get me started on actual command throws... someone does two light punches against my guard and then the camera suddenly shifts and a throw animation plays out that takes away a quarter of my health without any startup frames whatsoever? How do I even avoid that?
One thing I like and at the same time hate about Chun Li is how she has few "cheap" moves. I use that word reluctantly and in inverted commas because it makes me sound like a noob to call something cheap. I realize that every (?) blocked special can be punished or at least puts the one who blocks it at an advantage. But there's a lot of stuff that's easy to execute but requires good reaction, timing or simply knowledge to counter. Like all those characters who'll fly around at the top of the screen and suddenly come down in front or behind you, or just throw you, so you can't simply block it. Moves that confer immunity to fireballs, like Psycho Crusher or Tatsumaki. Even if you do block these, they often go flying off into the distance and almost out of reach again, or as with the Tatsumaki, follow up with an uppercut or throw so that it creates a 50/50 guessing game.
Some characters can stand at a screens distance away and just throw fireballs by doing the same motion over and over again, but advancing towards them feels like swimming up a waterfall. I need to time my FA-dashes and Hazanshus right just to get closer, and as I recover from getting past one the next fireball is already underway, this time from half a screen away. If I jump over it they'll SRK, if I dash through it they'll probably sweep, and so on. I realize that with good timing there's ways to get through to the opponent and attack them, but it's so annoying how I am always the one who needs to time her moves perfectly, lest I take a lot of damage, while the opponent is at no real risk. I have enough experience now that I can predict what a lot of people will do - what I lack is the timing, reaction or knowledge to properly counter it. So while the opponent goes through the same motions again and again, I'm at the edge of my seat trying to not mess up the timing and get in a few attacks myself which, in most cases, will be pokes that don't do a lot of damage. Incidentally, whenever I meet another Chun Li online much of this gets confirmed, because I never suffered from crap like what I mentioned above. Even when I lose, it just never feels "cheap".
What else is there? Perhaps the wakeup game, what little there is to it with Chun Li. As in... no options at all? Without any useful reversal, all I can do is block while waking up and then I'll have to endure their blockstrings and more pressure. Why do I have to endure that while people like Akuma can just teleport out of their wake-up, or create a guessing game by waking up with a Shoryuken?
When I first started playing I used Ibuki for a while, just doing a lot of neckbreaker and more or less randomly throwing out my ultra when available, or to punish a whiffed attack. I didn't even do that bad, just because of the sudenness and range of the neckbreaker that makes it hard to react to, it's ability to go past fireballs in it's EX version and because of the high damage super. Ibuki might not be an easy character to master, but she has a couple of gimmicks that can take you very far. Chun seems to be one of the characters who have really few gimmicks to rely upon.
What's holding me back, it seems, is my inability to deal with many other characters' gimmicks and "flowchart" methods that put them at very low risk while putting me under constant pressure. How do I overcome that?