For flaring, adjust so as the flare is just large enough to easily slip just the base inside the brass. You don't need any more than that. Too little and you might damage the base as with an unflared case.
For the roll crimp, it's really hard to feel with the loadmaster when using it progressively. Watch the video on Lee's website and then adjust accordingly. You want the die and seater adjusted just where it inserts the bullet to the right depth and a little extra effort on the handle pushes the case against the stop inside the die forming your crimp. You just want enough to roll slightly into the groove to hold the bullet.
I use my turret press (or even with the loadmaster one round at a time - ie non-progressive) for revolver rounds now just because it offers a little more tactile feel when doing the roll crimp.
I usually end with the Factory Crimp Die, just to post size the case in case it bulged a little from the roll crimp operation.