This sounds like a mechanical problem, not a hydraulic problem. It could be with the linkage between the shifter and the tranny, or it could be with the brake pedal interlock (though that would only affect getting it out of Park, not back into Park). I'd also discount the parking pawl sticking being the problem, as it should only be a problem shifting out of Park, not back into Park; even if the pawl were boogered up, that shouldn't affect shifting back into Park.
If you get under the car, you should be able to see the linkage on (IIRC) the driver's side of the transmission. I've never looked, so I don't know if it's a rod-type linkage or a cable-type linkage. If it's a rod, it could be bent, or the lever on the tranny case could be bent, or there could be some other kind of interference. If it's a cable, it's possible that the cable got kinked, or the sheath slipped in the clamp, or the clamp slipped and rotated, all of which would be relatively easy fixes.
If it's not readily apparent in the linkage, the problem is probably something damaged inside the transmission, but that doesn't seem terribly likely.