According to Fuudo, it's nearly impossible to surpass Daigo's skills. Here's a little excerpt:
When asked about Umehara: “His precision is very high. He’s the special one, like he has all parameters maxed. Beside incredible high precision, he also has strategies and reading ability. His safe jump is amazing. Even it’s Ryu againsts Sagat, I have never seen him missed. I think maybe it’s because 20 years experience. This’s why I gave up on surpassing him.”
Talking about Umehara’s experience: “It’s truely amazing. His basic techniques are perfect. No combo miss. He’ll adapt to it quick if he saw something new. He knows the tricks of all characters. Surpassing him is impossible. Just practicing what he did is difficult enough.”
On a side note, it cost him 200,000 yen to make it to EVO (roughly around $2,600)