The oil filter leak should be easy. The top O-ring is usually in the wrong groove if it's leaking. Make sure it's in the second groove and not in the top one. I tighten it with one hand first, then use both for the final twist. No more than that is needed. If the leak is from behind the cooler it's more complicated.

I bleed my brakes constantly because I road race my SRT-6. What works best for me is to bleed with old brake pads so the pistons are extended. If you don't want to go that route you'll need to do what the manuel tells you not to and pump the pedal with the bleeder closed using the 2 person method and then cracking the screw. Even then if the air is around the pistons it won't come out easily. I've put a gallon through the circuit with rebuilt calipers and new pads and in the end had to bleed with the old pads and reinstall the new ones once bled.

Les