Game 1: You simply get too many terminals.
I like the Watchtower, because it's great against Militia, Soothsayer and the expected Margraves. But the Moats are simply not worth the card slot they're taking. If you buy nothing on the turns you now got moat I think you're doing ok.
Game 2: Swindler is always a very nasty card. This set is obviously strong enough to build, but that also implies Swindler will wreak havoc.
Your money should come from playing Swindlers and having big hands, not from having golds.
Trashing down is not as good as it usually is, because this increases the chance of Swindler hitting your good cards.
If you can get big hands you can play your swindlers more often.
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I don't like opening Apprentice/Pearl Diver. Apprentice is bad for trashing cheap cards. The $5 should probably be Catacombs although Swindler is also an option. The $2 should probably be nothing. The Pearl Diver barely adds any value and could be drawn dead or be swindled into estate (Almost all cards that interact with the top of your deck by either revealing or selecting something can make pearl diver worth it, but here none of that is happening). Adding Pearl Divers later probably still is good, but I'd rather open Catacombs/- then Catacombs/Pearl Diver.
After that, try to get some Villages, Catacombs/Smithies, and 2 Swindlers you try to play as often as possible.
Only after you've got that going add Horn and/or Apprentice.
