As far as Dudley jumping in at Sim, I have had my anti-airs beaten or traded with so often that I think the timing and spacing is more specific for Sim to anti-air cleanly than it is for Dudley to beat it. This doesn't mean you can just jump all day carefree obviously, but beating Sim's anti-airs plus his command dash going through fireballs is a big help in getting close. Then you have the walk and block method, or focus dashing Sim's long range pokes.
I actually played Marn about a week ago and did much better than I thought I would. Almost got perfected in the 1st round, almost perfected him in the 2nd round. He started the 3rd trying to rush me but I was able to zone pretty well and chip him down to less than half life while I still had about 3/4. Suddenly he backs off to full screen and starts throwing out cr. mk, and just as I realized what he was doing it was too late; my st. fp was counterhit and combo'd into EX MGB (similar to Makoto fishing w/ cr. mp and comboing that into EX Hayate), and I was in the corner. One wakeup mixup later and I was dead. 3/4 life gone in an instant.
Now I'm as big a fan of Marn's Dudley and overall skills as anybody, but getting that counterhit into combo is not that hard. And it is an example of another tool Dudley has to get in, even from full screen. What really won that match for Marn though was his patience. If he had just continued rushing I likely would have won, but he smartly backed off and tried another way to advance and it worked like a charm. I'm curious as to what he would rate the match, I doubt he thinks it's as bad as 3.5-6.5.
Speaking of Marn, I thought his matches were the most entertaining at NSB 17. Unbelievably clutch stuff and amazing comebacks against Momochi and Machi. Dude is just crazy good at the game.