Hi. I assume you are the same person who asked this question on the Bristol Boat owners forum.
I also answered your question there. But because of a previous post here that might lead someone to do the wrong thing, I thought I best post here too.
I have a B 27. I have done this job recently.
Looking at your photo I would say that your packing gland hose does not look all that old. But I would say that if there is any chance that it is original equipment, or it is damaged.....it should be replaced. If this hose were to fail, you would be in a lot of trouble.
Now. About how to drop the rudder on a B 27.
There is a bronze pin that is about 6 inches long that fits in the rudder shoe and sticks up into the bottom of the rudder.
It is held in place by a brass bolt that goes from side to side. This side to side bolt is hidden. Look at this Picture
Sand off a little of the bottom paint in the area shown and look for the "soft putty" that is covering up this bolt. The bolt is brass so be careful but when you find the right spot, clean out the soft stuff to expose the bolt on both sides. After your remove the bolt, the pin will come out the bottom of the keel (rudder shoe).
If it doesn't "drop" out, you will need to use mechanical advantage. The pin has a threaded hole in the bottom. I think I remember that it is 1/4 inch. ... But it may be smaller. Here is a picture looking up at the underside of the rudder shoe.
Caution, the angle of the pin to the bottom of the shoe is not 90 degrees. You will need to make a wedge that will correct the angle of pull when you put the 1/4 inch bolt into the bottom of the pin. You should put a nut and large fender washer on the bolt that you screw into the bottom of the rudder pin. Then hold the bolt head with one wrench and crank on your bolt, you will to start to pull the pin out. (don't forget the wedge)
After the pin is out, the rudder will move to the side and drop down.
If you need more information just ask.