The grapple bonus isn't cumulative, is it? It's just a +5 for as long as you maintain.
The rules don't say what happens, but there are also no rules saying both combatants must be standing or prone at the same time so I see no reason as to why the grapple would break.
As for getting an AoO while grappling someone you can not make attack of opportunity.
Trips don't stop spell casting since there is no rule against spell casting while prone. I would have to check the rules to see if it even forces a concentration check. I imagine it would, but not as much as doing hp damage.
Sorry. You just have to learn the hard way. If you come from 3.5 many things are the same, but there will be times when you will be using a a 3.5 rule only to find that rule no longer exist.
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The rules about grappling are scattered around.
Some rule relevant to your questions:
Grappled: A grappled creature is restrained by a creature, trap, or effect. Grappled creatures cannot move and take a –4 penalty to Dexterity. A grappled creature takes a –2 penalty on all attack rolls and combat maneuver checks, except those made to grapple or escape a grapple. In addition, grappled creatures can take no action that requires two hands to perform. A grappled character who attempts to cast a spell or use a spell-like ability must make a concentration check (DC 10 + grappler's CMB + spell level), or lose the spell. Grappled creatures cannot make attacks of opportunity.As a standard action, you can attempt to grapple a foe, hindering his combat options. If you do not have Improved Grapple, grab, or a similar ability, attempting to grapple a foe provokes an attack of opportunity from the target of your maneuver. Humanoid creatures without two free hands attempting to grapple a foe take a –4 penalty on the combat maneuver roll. If successful, both you and the target gain the grappled condition.
Grappling or Pinned: The only spells you can cast while grappling or pinned are those without somatic components and whose material components (if any) you have in hand. Even so, you must make a concentration check (DC 10 + the grappler's CMB + the level of the spell you're casting) or lose the spell.
Grab (Ex) If a creature with this special attack hits with the indicated attack (usually a claw or bite attack), it deals normal damage and attempts to start a grapple as a free action without provoking an attack of opportunity. Unless otherwise noted, grab can only be used against targets of a size equal to or smaller than the creature with this ability. If the creature can use grab on creatures of other sizes, it is noted in the creature's Special Attacks line. The creature has the option to conduct the grapple normally, or simply use the part of its body it used in the grab to hold the opponent. If it chooses to do the latter, it takes a –20 penalty on its CMB check to make and maintain the grapple, but does not gain the grappled condition itself. A successful hold does not deal any extra damage unless the creature also has the constrict special attack. If the creature does not constrict, each successful grapple check it makes during successive rounds automatically deals the damage indicated for the attack that established the hold. Otherwise, it deals constriction damage as well (the amount is given in the creature's descriptive text).
From all the above, you will be capable to make a AoO only if you have the Grab ability (or some equivalent ability from feats or archetypes) and take the appropriate modifiers to your CMB when grappling someone.
You can check this thread: What are some things about the Pathfinder rules that you think most people don't know?. Don't be daunted by the 1,010 posts. If you skim it you will find the sum-up posts that Hovie23 made. He stopped halfway but his posts cover the most important topics. Very useful as a sum up of obscure rules.
Here's how I would run it.
I was wondering the other day, suppose a mind flayer has a death grip on an ally (or any other 'grapple this round, kill you in the next') and you're going nuts trying to break him free. What would happen if you trip the grappler? This question is still applicable in any case of grappling. Do they both go prone?
Nothing implies that both have to be prone and the rules still work if one is prone and the other isn't. So, the tripped grappler is prone and nothing happens to the defender.
Does the grappled guy get any bonuses on his next CMB to break free?
No. While melee attacks would be at a -4 penalty for being prone, there are not any penalties for combat maneuvers.
Note that a character always has the option to use the aid another action to grant a +2 bonus.
If the grappler doesn't gain the grappled condition (I believe there are abilities, feats and one or two other ways to grapple without gaining the grappled condition) does he still get the chance to do an AoO against the guy doing the tripping?
Sure as long as all the normal requirements are met you can make an AoO.
Also, is a trip going to stop a spellcaster in mid-cast (say for instance I used it as a readied action) or do they still get a concentration check and can continue casting as normal, even after they've been laid prone (I blame video games for making me consider this)?
The rules don't specifically say, so by a strict RAW this would be no check required. I would however consider being tripped as equivalent to either being attacked successfully attack for zero damage or in the same category as 'vigorous motion.' Either of which would call for DC10 + spell level concentration check.
Also consider that his line-of-sight may be affected by his new outlook on life.
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Here's how I would run it.
I was wondering the other day, suppose a mind flayer has a death grip on an ally (or any other 'grapple this round, kill you in the next') and you're going nuts trying to break him free. What would happen if you trip the grappler? This question is still applicable in any case of grappling. Do they both go prone?Nothing implies that both have to be prone and the rules still work if one is prone and the other isn't. So, the tripped grappler is prone and nothing happens to the defender.
Does the grappled guy get any bonuses on his next CMB to break free?No. While melee attacks would be at a -4 penalty for being prone, there are not any penalties for combat maneuvers.
Note that a character always has the option to use the aid another action to grant a +2 bonus.
The prone -4 penalty apply to the CMb too, thanks to this line in the rules:
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.
A CMB attack fall into the more broad definition of melee attacks [you could use the in game meaning of the term, i.e.Melee Attacks: With a normal melee weapon, you can strike any opponent within 5 feet., but then the penalty would not apply to unarmed attacks and natural attacks and that is a bit silly].
Note that penalties to AC apply to CMD, so if the the controlling grappler was knocked prone and the other grappler wasn't, the -4 AC should make it easier to escape.Does the grappled guy get any bonuses on his next CMB to break free?No. While melee attacks would be at a -4 penalty for being prone, there are not any penalties for combat maneuvers.
Note that a character always has the option to use the aid another action to grant a +2 bonus.
You're right, I was too narrowly focused on any bonuses.