Transfers will go over a smooth finish better. They'll stick better, and over a very dull finish you can get "silvering," or whitish discoloration of the transparent parts of the decal.
My experience is that there is such a thing as "too much" gloss. It seems like a decal needs enough texture to bite into something, but not too much that you get silvering. Semi-gloss works fine.
I use solvents to soften the decals and make them seat better. This works fine, but the solvent can attack the paint itself, so I usually clearcoat before the decal, and after to protect it and provide a unifrom finish to the model.
If you do clearcoat beforehand, you can spray it on and let it dry thoroughly, or you can brush it on (which I usually do). If you do brush it on, you may want to paint the entire area/panel/piece that it's on, not just the part it's going to sit on, because even after other clearcoats, you might get a patch of different finish, which will look bad.
As far as the Ork decals go, it's hard to find many good uses for them, as there's rarely clean, open spaces on Ork gear to mark. It's a shame, cause they're nice looking, but there's not many good uses. The checks will probably be more of a hassle and ultimately look worse than some careful hand painting, especially if you're not already an old hand with decals.
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