Pic,
There will be several opinions on what the best approach should be.
That being said, people in the boat service industry will tell you(example: a deck fitting) to apply the caulk liberally(up to 1/4" thk.) & set the mounting base onto this. Tighten the bolts/screws until the chalk begins to squeeze out (I leave the caulk thickness at about a 1/8"). Clean the squeezed-out caulk around the fitting & wait.
Different caulks have different setup times. Follow the manufacture's instructions before tightening the fitting down. When doing this you will have alittle more caulk squeeze out & just dress this. The caulk will not be setup fully underneath the base & this is what will squeeze out. I always use a flexible caulk (Dow Corning 795)for my shrouds, stanchions & other fittings which take stress. I'm looking forward to using Butyl next based on Mainsail's advice.
Now, you have a bedding with a substantially thicker gasket. Why apply caulk & tighten down while watching most of the caulk you just applied squeeze out. What you will be left with is a very thin seal. I know I'm gonna take some heat for this, but I can tell you that what I bed, I don't have to pull it up & re-bed it again.
I also don't use 5200 above the waterline on exterior surfaces. UV will harden and your bedding will show cracks. Plus, it's not flexible as other caulks & a ***** to remove. Then there's Butyl tape that works well with no messy caulk cleanup. The choice is yours my friend.
CR