Why are you talking off the wheel to remove the caliber ? Once you have the caliber back on, remove the brake line and induce compressed air into the caliber to move the piston out in the caliber. Sometimes if the piston's all the way depressed, it will produce an air lock and won't let enough fluid in. Also like mentioned before, make sure you didn't twist the rubber seal in the caliber.
2010 FLTRX , Stage 1, 13" Madstad, Mono tubes, SuperShox, Heritage style bars. Alpine CDE-HD149BT,Soundstream Picasso Nano Series PN4.520 , 5X7 and 6.5 Infinity Kappa speakers
If I have to explain ,you wouldn't under stand anyway.