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1) Do you level your guys up SIGNIFICANTLY higher than what’s expected for the current level/boss?
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Yes, always. In Final Fantasy Tactics all of my characters were at level 60+ before the end of the first chapter. In FFVII, all of my characters were at least at level 40 before the end of the first disc.
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2) Do you level your guys up so they can fight the boss on more “equal” footing, but still have some difficulty?
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No, I level up as much as possible. That Ice/Fire dual dragon head boss in FFVII, the FAQ I was reading said he was very difficult. I killed him in three hits.
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3) Do you level only certain party members in which ever RPG you might be playing, or do you go the full nine yards and get everyone maxed out?
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Everyone, unless they really suck. It was easiest to do this in Final Fantasy X, where you could easily switch out party members during battle.
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4) What RPG do you recall has having the longest time spent on pure leveling up? Alright, running to the local town to restock supplies you can count, as long as it’s mainly just raising the level of your characters?
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FFX. I took (and take) the time to use every character in EVERY battle (when possible). Just before the battle with Seymour on the Bevelle highbridge, I spend an hour or two fighting all of the machines that show up. They are very easy to kill and give a
LOT of sphere points. I max out everyone's sphere grid and learn all of their attacks before fighting Seymour. Then I kill him in two or three hits. Next would have to be FFVII. I fought grasshoppers in that mountain cave (first disc) for hours and hours. The majority of my levelling up was done there.
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5) Do you normally level up in every RPG you play? By that - ie grinding like an over-worked bitchy mom.
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Yes, always.
Jam it back in, in the dark.