It sounds a bit like Stronghold or Stronghold Crusader. In both of these games, you have an advisor who communicates to you the current status of your castle and if more resources are needed.
I'm pretty sure the first game you're describing is part of the series of games based on the "Zoombinis." I remember playing the first one as a child too! Fun game :)
Wow man! I think I've been looking for the same game for about 10 years!!
This is what I remember:
- The game title definitely had a year in the title (like you said), and I remember there being "Alien" or "Aliens" or maybe "War."
- I remember it being either shareware or freeware...
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