I'm not crazy. My mother had me tested.
So ... Caltrops says it works against a monster. Does it also work against Henchmen and/or Villians? Or does it only work against 'monster' type only?
If the villain or henchman says monster above the check it will work.
Second question. Example: For Kyra one of her skills is Wisdom, and under it is Divine: Wisdom +2. If she has to do a check for something that just says Wisdom ... is it a straight up roll or a roll with the +2? I'm assuming it is only a straight roll but wasn't sure.
She does not get the +2 since it is not a Divine check.
Last question isn't a rules question. What is generally considered to be best practice when leveling up a character? Pump up the stat you are weakest in, in order to help with those checks when they come around? Or focus on your main combat skill type?
My opinion is to use your first two skill feats to pump up the skill you use to fight monsters. After that you might want to increase a skill that has a secondary skill attached to it or continue increasing you combat skill. For example, Valeros has diplomacy under his Charisma so you may want to increase that skill. The other players in my group almost always max out their combat skill before branching out.