Observations

• Try running a mission below 20%, the game won't even allow you to. Probably to prevent people from trying to luck themselves into getting early medals.
• The lowest success rate for missions is 1%, there was a screenshot of someone who still had Kanna at her base stats but already had the mission.
  • Success rate seems to be determined by the percentage of the total stats you have required for each mission.
    • e.g.: If a mission requires 50 DIV and 30 DEX, and you only have 40/50 DIV and 20/30 DEX, you'd have 60/80 stats, which equates to 75%.
    • This also means you don't need to cover al stats completely in order to reach 95%: Like so (40/42 stats = 95.23%)
    • Another example is here, in which I had 85/2700 stats, which is 3.15%.
• Training bonuses appear to be somewhat random but can still be triggered even if it's not the Squire's specialty or you haven't gone out with them, it just increases the chances for it to happen.
• "Subtle Hint" probably means the hints Squires give you (Dai and Eirlys). While it isn't entirely needed, it is still useful in case you're trying to find out where you are in the sequence.
• Logan's quests may be more tedious, but he has the better Speciality for most missions as they often require more DEX than DIV (which is Kanna's Speciality).

There are already several spreadsheets and even a fancy tool for managing squire answers, it's just a matter of actually wanting to put that here on the Wiki.

Can you give me a link to the fancy answer managing tool?

Also, counseling removes all stress entirely.

http://mabinogi.tsundere.fr/squires.html

Your progress saves even if you close it, a more detailed explanation shows up when you click the "?" at the top.
(Also try hiding Logan, poor guy)