The Legendary Pixel Crew

I'm not sure how "rapid" the succession needs to be, but a 3.5 wizard should be able to do it at 2nd level. Unless the first target perceives the second casting as a threat, there should be no problems.

Well, unless they have exactly 11 intelligence, they can do it at 1st level (or if they specialize in enchantment). Though, a wizard with 11 intelligence isn't really a wizard and more of someone who doesn't know how classes work.

Well 11 INT could be a NPC who decided to be a town wizard instead of an adventuring hero. He's smart enough for 1st lv spells and if he's a specalist (banning necromancy is a no brainer for this kind of build) he has 3 spells per day he can use for things like leomond's chest, make whole, continual flame and crafters fortune to eek out a modest living.

both continual flame and make whole are second level spells though.

Not to mention that the 50 gp is abit steep for most commoners. still worth it for any innkeeper though... guess that one is one of those "it takes money to save money" kind of things.

Boloney wins again! All hail the glorious puzzle maker!!!

if it's in 2 consecutive rounds than any caster capable of casting enchantment spells could throw 2 of them out.

If it's ONE round then in 3.5 there's a couple ways it could have happened, Either a specialist Enchanter with Metamagic school focus (enchanment) could have thrown out a Quickened or Chained charm person from a 3rd level slot or they could have taken Arcane Thesis (charm person) or Easy Metamagic (quicken spell)

In Pathfinder I can think of only one way to pull this off in one round at lv 5 and that's Magical Lineage (charm person) but that would mean he's built SOLELY for rapid casting of charm spells.

Maybe the first cast takes place during a suprise round, and the guy ends up first place in the initiative order so he can cast again before anyone else can act?