Before I would go any further, like prowlersfish said, I would carefully clean off the rudder shaft so if the bearing moves, it does not trap any rust or grit and causing galling. It might be worthwhile to try an extremely thin penetrating oil like 50/50 acetone/ATF or even go 75/25. Be careful as acetone is almost as flammable as gasoline.
Are you sure the bearing is seized to the collar? It seems much more likely they are both seized to the shaft.
If you have somebody to help you, have them push up on the rudder from underneath the boat and see if it moves up far enough to get a puller on the bearing. It might help to pull the gland nut and remove the shaft packing to free things up. If you can do this, you might be able to pull both at the same time.
You also might be able to get a wedge between the oak and the bearing and displace the oak far enough to get a thin jaw puller under the bearing. Of course, you need to be careful to not damage the oak while doing this, but it should be flexible enough to push it down 1/4" and get a flat puller jaw in there.
Kind of hard to see everything from the pictures, but it might be worth putting a piece of aluminum or brass on top of the shaft and hit it with a drilling hammer. Not so hard you damage the oak board, but enough to impact the joint between the bearing/collar and shaft. If it moves, you might be able to slowly move the bearing up far enough to get a puller on it. Or, if you have them free, you can put a pipe large enough to clear the collar over everything except the bearing and be able to drive the bearing back down far enough to get a puller between the bearing and the collar.
Another option is to find a bearing separator like
http://www.harborfreight.com/automotive ... -3979.html. If you go with a cheapie like the HF one, be careful because they are made of pot metal and can fail spectacularly. That should separate the collar and the bearing far enough to get a puller in between.
Have you ever noticed that when things are easy to get to, they never get stuck?