Hmmm, some differences of opinion on how much one should grind.
My opinion is that when you are going through Tartarus, you should go through each floor and fight every enemy you find (unless you've explored the whole floor and they're reappearing, they will do that after a few minutes, then you can avoid them on your way back to the stairs). If you do that, you should be pretty well covered and not under-leveled -- especially if you take XP bonuses from Shuffle Time. On a first playthrough I generally like to go to Tartarus either once per week or once every two weeks. You may also want to wait for a call from Elizabeth/Theodore about missing people in Tartarus to go in for the first time in order to avoid backtracking a bunch (though I wouldn't rely on that because in some months he doesn't call you until quite late).
Shuffle Time is different in P3 than in P4 (which I'm assuming you've seen from Edurance Run). You can get weapons, money, XP bonuses and healing as well as new personas from it. You should definitely use this to your advantage, especially if you want to avoid being underleveled. Here's what I'd recommend:
1. If you see a Persona in shuffle that you don't have yet, take it first. Even if you aren't going to use it, you can always take it to the Velvet Room and fuse it to make something more interesting (note that any persona that you add to your lineup through shuffle time will be automatically registered in the compendium if you haven't already fused it). If you run out of Persona slots, you can always replace the new ones you find with other basic ones in your current lineup and buy them back later from the compendium if you need them for something.
2. If you have the personas in the shuffle already, take XP bonuses. This will decrease your need to grind considerably.
3. If your protagonist needs some healing, take the cup cards -- there's a chance it'll heal your whole party, so it's useful if you really need it. Though I find that the clock and your items/skills are better for this. It's okay in a pinch, though.
4. After you've got the available personas and you feel like you're not getting all that much XP from your battles (or enemies are running away from you), take the weapons or the money. The weapons are not the current best weapons you can get, but loot is loot, and you'll need all the money you can get.
For the life of me, I've never been able to figure out exactly what conditions you need to meet to get shuffles, but I know for sure that you will get a shuffle when you finish a battle with an All-Out attack, or when your protagonist lands the final blow in a battle. You'll sometimes get them in other situations, but I don't know if they're just random or if there are other conditions for them.
Also, one last battle tip. Do not lounge around on one floor for too long -- you cannot just sit on one floor, wait for enemies to reappear, and just grind a bunch in one place. Bad things will happen ;D Try it out once just to see what happens, but you'll probably want to avoid it until close to the end of the game XD
Whew, long post is long, sorry for all the rambles D: Hope that's helpful, anyway.
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