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A party going against a challenge that is equal in CR to the APL should have a fairly easy time overcoming the encounter. This is skewed even more against single opponents, as the party has an advantage in number of actions.
Remember that you are putting 6 people against 1. Would you expect a single soldier to be a challenge for a squad of 6 enemy soldiers without some serious luck or tactics on the part of the soldier?
You may want to use multiple weaker enemies that equal the same CR of the single bugbear, but remember that weaker CR creatures are easier to defeat one on one, thus you will most likely end up with a similar curbstomp, despite everyone having their own opponent.
If you want a challenging encounter, you need to have the enemy CR be higher than the APL. However, keep in mind that not every encounter must be a tough one. Give the party chances to feel like powerful heros by throwing enemies they can wipe out without breaking a sweat.
Hi there! I've been playing for a while in a party of 5 (+1 GM, so 6 people) and (although we keep swpping GMs) we've also found that CRs for a party are difficult to gauge.
Remember that a CR2 equivalent encounter is only supposed to be an average encounter for your party. If you want to actually challenge them, then you can always up the CR (to about APL+3/CR5 in this case, but that's classified as an epic encounter, so you should have at least one near death experience). We have found that with 5 characters, the average encounters are a joke. Also, check how the XP is divided up in a party of 6 (I think it's just XP/6, but I can't remember)
The best thing to do would be to add more lower-level enemies, as a large party can often handle single opponents well to a point. Eventually, the BBEG you throw at them will be a challenge for the party as a whole, but any one character who gets hit by it will be taken out of combat. You can even try adding 6 orcs (1 per player), but also remember that you are responsible for the initiative order, and keeping 6 players motivated while managing 5 or 6 orcs isn't the easiest thing. (but a big party is going to be a challenge anyway if you are new to pathfinder)
I would recommend 2 or 3 CR2s (2 to start with, in case they're harder than you think), as they will be tougher than orcs, they probably won't decimate the party and they won't hog your time with keeping track of initiative.
While the phrase is a bit overused it still holds true - these rules are only guidelines (and you got them right).
Example:
Your party of 6 contains an optimized Barbarian with 20 Str wielding a masterwork Falchion.
He will have a +8 to hit and thus need to roll a 9. He does 2d4+8 damage - or 13 average. On a max roll or a crit he will onehit the Bugbear!
BUT if your party is in for a round of bad rolls, consists of fairly non optimized characters and the Bugbear has a chance to single out a Wizard and bring in two good hits you may even have a dead (as in con score of negative hitpoints) party member (but this is fairly unlikely).
So at these very low levels much is dependant on the rolls, the characters and the situation.
That said I would bring 4 orcs of which one is a level 2 Warrior as a challenging encounter - give or take an orc depending on your PCs optimisation level.
Yes.
Funnily enough, you chose one of the weaker CR 2 creatures (A CR 1 human barbarian 2 is tougher usually) and some of the stronger CR 1/3-1/2 creatures. The Orcs might be a decent battle, depends on if a Color Spray/Sleep takes out a major chunk. The Bugbear won't be. Ever.
Generally, quantity (monsters) is better vs. quantity (PCs). If you raise the quality (CR of monsters) vs. quantity (PCs), the damage could be too much (i.e. Villain's Fireball/stone gaze vs. 6 below CR PCs and Fireball/stone gaze vs. 4 at CR PCs) and/or the AC may make the villain unhittable to 3/4BAB classes.
If no such imbalance is there, low numbers of foes, even at higher CR, will have a hard time against the many actions of such a large party. It'll swing the opposite way really fast. You can still find a balance, it's just harder.
So stay about even for CR and just boost numbers until you get a sense of the differences.
This should work most of the time, but you have to be wary of clumping your villains. Try to have at least two battlefronts where possible. Aid with corridor/room design allowing them to circle around/surround, so they aren't "Fireball/Stinking Cloud/Combat Reflexes fodder".
So, yes, you have the guidelines right, and yes, your suspicions that the guidelines are not hard-and-fast rules is right, too.
You should do fine with such instincts. :)