I have a Pearson 36-2 and have had the rub rail replaced.
I cannot speak to the detail of the repair
(it was included in the repair
of the deck at the chain plates at purchase) as I did not do it myself but did observe some of the work and do most of my repair
work where indoor facilities or special tools are not required.
This said, It is fairly straight forward and I did talk with the shop that did mine.
The 36-2 has an outward hull to deck joint flange. the rub rail itself is an L shaped extrusion that hangs over the joint (upside-down L) and is fastened with through bolts through the teak toe rail. Since the L section is wider than the joint itself, it easy to bump it and break it because the L is has no supporting material behind it. I have seen this breakage on several other Pearson's of the same rub rail design. If I had the funds, I would bolt on an aluminum toe rail
There is a second smaller L section cap that is screwed from beneath to cover all the bolts from the bottom side with wood screws. It is screwed in at more of an upside down V with screws at the V point to cover the bottom through bolts)
The best place to observe the assembly is at the stern because it does not have the smaller L section cover cap and you can see the through bolts, and the overhang of the rub rail L section.
To remove the rub rail you will need to remove the entire teak toe rail or as far is you wish to scarf a section in, save your bolts.
When mine was removed, there was no caulk however I would suggest using 4200 when replacing it as there is many opportunities for leaks to form from the flange seal, the through bolt holes and the backing L cap that screws right into the bottom with wood screws (not nice as it is blindly screwed).
My 36-2 does have leaks, so the wholes assembly is suspect. The good thing is that you can reach all of the bolts from the outside unlike most bolts which have an inward flange.
If you do have leaks on the inside of the boat at the hull to deck joint you can observe the factory caulking from the inside . A good place to do this is in the port side lazaret, lots of space to get a look at it. If you notice caulking gaps, do not be surprised. You may be able to caulk a bit from the inside as I did in some places but it is best addressed from the top or in the joint itself .
Keep in mind, most water running off the deck runs into the rub rail extrusion then goes to the lowest drain near the cockpit coaming. Since water can reach the Rub-rail extrusion, it can get under it so... caulk it.
I wil be replacing toe rail in the off season, so if I remove the rub rail i will try to post pics.