2) if expectation is to lose 25k, to beat it by 40k you 'only' have to win 15k. That means winning 5018 times (5018*400 - 4982*400 = 14400)
Using your numbers, he would be about 8.8% to win 15K or more. That's based on his winning 5018+ out of 10K rolls, with a 49.5% chance to win each individual roll. That's obviously in the realm of possibility.
My understanding is that he has played more than 10K rolls, but the fact he varies his bet sizes adds more variance. As someone already mentioned, some kind of Monte Carlo simulation would be the best way to figure out how probable his win streak is.
I have read about this situation, but I have never even been to the just-dice site so I don't know how the games work. Is he always betting the "even money" type propositions? Can you bet stuff like "over 25.5" at close to 3-1 odds? How many different types of bets can he make? If he's betting a wide variety of propositions, setting up an exact simulation of his bets is not going to be easy.
If someone does go through the trouble, they should obviously run it more than 10K times.