You should be able to tell where the hull will leak by looking at it. If it is seamless, all joints sealed with polysulfide and painted, then there should be very little water in that bilge. If you see any open joints then all bets are off. If there are open joints they can and will get wet and when the wood swells up a bit then they have a tendency to seal themselves on occasion, however, you really don't want to rely on wet wood to do the job.
Lifecaulk, by Boatlife, is a really good one part polysulfice sealant, but you will need to wear a couple layers of the disposable gloves if you're going to use the stuff. It is nasty to get on your hands. When the glove gets all gooped up and you feel like a tar baby, peel off a layer and continue with the work.
Another thing to watch for is areas that need to be refastened. If there is any loose hull fasteners, they will cause the skin of the boat to work against the stem of the fastener while you are under way and this can cause a point of entry for water. Use the right kind of fastener from Jamestown Distributors (silicon bronze or stainless steel) plug the holes with a mahogany bung set with Lifecaulk and go boating!
The rudder log and shaft logs will leak just like any other boat if they are not properly fastened. On a wood boat you have a wood substrate and that has to be in solid condition so that bears inspection. Any rot will have to be sliced out like a surgeon and replaced with new wood, properly sealed and fastened. It's part of the work (and the fun, but more on the work side) of owning a wood boat. If you are lucky there won't be too much of that, but you can expect some.
Regards,
Paul