Notice:
The advice given on this site is based upon individual or quoted experience, yours may differ.
The Officers, Staff and members of this site only provide information based upon the concept that anyone utilizing this information does so at their own risk and holds harmless all contributors to this site.
John, You start drilling and inserting screws at either end. Have a second person above pull the rail to the right position for each additional screw. Make sure the rail is centered over each hole (you can accomplish this by simply drawing a line fore and aft of the hole) else you'll risk splitting it. Good luck.
Unless your deck is discolored so that the original rail location is obvious, I'd draw a light pencil line around the existing rail where it meets the deck. This will make lining up the new rail a lot easier.
And yes, start at one end.. bending, drilling and putting in one screw at a time.
Getting the unbent rail bedded in may be the fun part.
I don't know if I'd try applying caulking as you're going or wait until the entire rail is in place, then apply bedding by backing the screws out a bit and raising the rail would work out better. I'd lean towards method #2 myself.
Either way, this part will get very messy. Have plenty of paint thinner and rags handy to clean up the caulking. One dab of bedding compound will spread to cover the entire boat.
(I use 3M 101 for this kind of application.)
Currently maintaining two holes in the water...'77 Venture 23 and new to the family, '78 Catalina 25
Notice: The advice given on this site is based upon individual or quoted experience, yours may differ. The Officers, Staff and members of this site only provide information based upon the concept that anyone utilizing this information does so at their own risk and holds harmless all contributors to this site.