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Simply does combat maneuver bonus or defense become modified under certain conditions? Does armor check penalty mess with these or does a bless spell add to your chance of success?
Specifically does the check penalty from wearing Plate armor damage your ability to grapple?
When you attempt to perform a combat maneuver, make an attack roll and add your CMB in place of your normal attack bonus. Add any bonuses you currently have on attack rolls due to spells, feats, and other effects. These bonuses must be applicable to the weapon or attack used to perform the maneuver. The DC of this maneuver is your target's Combat Maneuver Defense. Combat maneuvers are attack rolls, so you must roll for concealment and take any other penalties that would normally apply to an attack roll.
Some feats and abilities grant a bonus to your CMD when resisting specific maneuvers. A creature can also add any circumstance, deflection, dodge, insight, morale, profane, and sacred bonuses to AC to its CMD. Any penalties to a creature's AC also apply to its CMD. A flat-footed creature does not add its Dexterity bonus to its CMD.
Armor check penalty applies to all attack rolls if you are not proficient in the armor in question. Since a combat maneuver is an attack roll, it takes the penalty as well.
Bless provides a morale bonus to attack rolls and thus helps your combat maneuvers since they are considered attack rolls.
Followup to that question then. So say the monk grapples someone. When that person attempts to break free of the grapple are they at a -4 assuming they do not have unarmed strike?
Everyone has an unarmed strike. If you were referring to proficiency or some such thing, then know that, that has no bearing on grapple checks since grappling doesn't require or involve weapons.