try looking for quests that are redo-able like "Reagent run" or doing Clan trials to get better Clan abilities.
What boss is this? You get the random encounters a bit later I think

 

In FFTA2, Abilities > Level.
There are repeatable quests. Some quests involve no battle so you only get AP and no EXP. So pick the quests depending on your training needs.

Also there are clan/monster random battles, you need to progress through the game a little bit. Enemy clans appear after you win some auctions. I'm not sure about the exact condition of random monster encounters but I think they appear before you can do auctions.

You don't randomly encounter when you're walking around in an area; Instead, when you visit a new area or complete a quest, there's a chance of monster enemies/hostile clans appearing.
Some of these battles are kind of a semi-quest on their own, for some monster battles reward you with a specific reward and such.

 

its the opposite for me. my generic characters are overleveled, and my main characters are a bit underleveled. this is because every chance i get i choose to disbatch for quests. if you can complete the disbatch, which takes under a minute of walking around, the guys you sent (usually 6) get like 60 exp automatically and everyone in the party gets 30 ap. since you can't send main characters on disbatches, they get underleveled.

 

Can you get more than 6 people per battle? the cap sucks

 

your guys have to be a high enough level to not fail, usually you need them to be as high as the quest level i think. And i don't know if this helps but i always put the highest level character i'm sending as the leader.

edit: oh and i think you can tell whether or not you'll fail by if the guys that are going (but not the leader, and also have to be a male race - hume, bangaa, seeq) so you look at those guys that arent the leader and if they like have their arm raised or maybe are jumping up and down or something you should be able to complete the quest. idk why but the female races always seem to bow their heads...

 

Filling up the MVP meter helps them do better at dispatch, character level should at least match the quest level I think, better if you dispatch the recommended Job.

For the person with sucky items, try using the bazaar. As far as I know its the only way to improve what the shop sells in the early game.

I haven't gotten to the dragon bosses yet so, I can't help you with that try doing some other quests to level and to learn abilities before tackling it again.

PS I agree that Abilities > Level

 

Has anyone figured out who to send on the sidekick quest for the historian? I have sent every single person I have and nothing seems to work. I think the quest is a level 14 and I have sent level 30+ characters including a time mage, sage and a few other job types of similar level. I can't seem to figure out if I just don't have th right job type yet.

 

Ah, no wonder. A ranger is one of the few types I don't seem to have yet. Thanks!

Another question: what clan trial gives you a speed increase? I have maxed out all clan abilities by just doing quests, but I did not go though and do every single clan trial. Working through them now, but they are tedious because of the sometimes impossible laws (>20 damage!).

 

Would asking to trade for some good weapons be frowned upon ? ;D
I hate using the Bazaar (even though I got the Sleet Rod and Thunder Rod !)

 

i traded with my cousin once and i got the dual wield sword for ninjas i was really happy. thats the only trade ive done though and i probably won't do it again.