Mark,
Regarding "tips, tricks, and advice", there really are only two types of caulk that should be used on a boat: polysulfide or polyurethane.
Polyurethane should be used to bond two surfaces together that will probably NEVER have to come apart again. Polyurethane is strong, and will not let go. Once two surfaces are caulked with polyurethane caulk, it will be really hard to get the two objects apart.
Polysulfide should be used everywhere else. Chain plates, stantion bases, under hardware, etc.
IMHOP, Silicone should NEVER be used on a boat. Silicone goes on easy enough, but looses it's grip in a few months, and attracts dirt. If you have any silicon caulk on your boat, rub it with your thumb and watch how easy it comes up. If you have any leaks, 9 times out of 10 silicon caulk will be present near where the leak is. The stuff just has very little use on a boat.
Use either either polyurethane for permanent bonds, or polysulfide for everything else.
