I have had the same problem with both 290's that i've owned.Neither regular riding or oil changes make any difference.There are two ways to get things freed up:
1-rock it in a high gear with the engine dead as described before.
2-Rev the nuts of it in neutral,clutch in [i'm told it distributes the oil],let the revs drop to idle and engage a gear as normal.My mate showed me step 2 but would only do it on my bike, never his own Sherco ....strange !