As for the upgrade it's pretty much a crapshoot. You might get one but don't count on it. Most of the inside cabins are pretty much the same so you will have a great cruise whever you are assigned.
8 Norwegian: Sky, Jewel, Dawn, Epic, Pearl, Breakaway, Getaway, Escape
10 Windjammer: S/V Legacy X3, S/V Polynesia, S/V Caledonia, S/V Diamant, S/V Sagitta X2 S/V Mandalay, S/V Vela