To be clear, your computer will never use the term "memory leak". That's just what we call it by. The message you'll receive when you crash due to a memory leak is the one you gave - "TLOPO.exe has stopped working". As far as the docking situation goes, docking is a common crash-causer because it's one of the most stressful activities the game performs. Docking at, say, Outcast Isle is a simple task - it's a small island with few enemies, no buildings you can walk into, very little overall surface area, and the real kicker - few people (usually). This, of course is the situation with most wild islands - there's not much to load in, so your system can probably handle it without crashing. But loading in big areas like Port Royal, Tortuga, or Padres del Fuego is a very different situation - lots of enemies, people, buildings, surface area, etc. You'll notice that these crashes also happen when you come out of a small building like a tailor shop and re-enter one of those bigger areas.
Basically, the reason this happens is because the system uses the memory, but doesn't dump out what it no longer needs. This accumulates over time, most notably when you transition into an area that has a lot to load in. I personally struggled with this a lot before recently. I would crash after loading 2-3 large areas and could never dock at big areas when I had loot. What changed is that I put my graphics to custom and set everything on low/unchecked. There are some other things I do to reduce memory waste, but I think that's probably the biggest one. If you do already have your graphics at custom>low, then the only other setting you should change is to turn your music and sound effects completely off.
Hope this helps.
