There was a very good article on this within the past year or so in Passagemaker. One of the things they mentioned was using a copper paste called KoprShield on the wire end before crimping the terminal on. Another was using heat shrink tubing. I do both wherever possible.
It is very difficult to seal these ends, even with KoprShield and heat shrink tubing. Corrosive salt air will work its' way in there sooner or later, which is why on older boats you end up with all these powdery green terminals way inside the boat where you didn't get liquid water. In the areas of the boat that DO get wet, the problem is worse. I think it might be worse on the coasts where the water is salt or brackish.
The strain spec is, I think, fifteen pounds. Ancor and ABYC have a lot of this in their literature. It's interesting: much of marine wiring is performed when you're crammed into a console or pretzeled in someplace that's hard to get to. Most of the boats here are larger than mine; okay, they have more wiring to service but there's more room to do it. As the years have gone by and I've gotten thicker and less bendable, my appetite for squeezing in to service wiring and plumbing has diminished. So I'm trying not to do this stuff over too many times if I can help it.
All of this adds up to trying to get the most longevity of service out of the wiring I do put in, and the best reliability. I haven't had any difficulty with Ancor wiring or tools, although other companies make marine cable that is just as good. (Oceana here sells a generic brand of tinned cable in some sizes that looks identical to Ancor and I've used that a few times.) The Ancor tools and cable ends are first-class. Obviously they have this stuff made up for them, but their specs are high-end and their products are reliable. Also their catalog is readable and you can find what you need.
One other thing: when my boat was built, Hatteras roughed in extra circuits to the flybridge console in case they were ever needed. I do this when I am pulling wiring through in difficult areas; either I use cable with more strands than I need, or I pull extra cables through and just shrink-wrap the ends, against the time that I may need them. Sometimes I end up using them, sometimes not, but it saves time later on.