I honestly can't testify too much to your second dilemma. I grind the hell out of my characters in single battles that I stretch out to great lengths just Accumulating to gain JP until I'm ready to end it. I've never really noticed the issue of being out-geared. This may be because I probably seriously grinded mid-to-late game where gear gates weren't an issue anymore. It may have played out in the all-or-nothing gameplay I notice at the end, where it's all about spamming your overpowered attacks before the enemy does theirs. Another problem I had is that FFT is just a really hard game, so I always felt grinding necessary, and while I'm a big advocate of pacing, the game was just so good I didn't care that I was wasting entire afternoons on a single battle unlocking a couple job trees.

I'm not sure if you've played Tactics Ogre, Sky, but the system there is arguably even more open than FFT. There's no primary ability slot, secondary slot, move slot, or support slot. There's just a massive list of hundreds of skills, passives and actives, for each character to buy from and assign to 8-12 slots (which you also have to buy). It might just be the kind of player that I am, but I get absolutely enthralled in this extreme of customization and its probably why I liked FFT better than its successor.

I didn't like FFTA's progression system of learning abilities from equipment. It wasn't as well-executed as FFIX because the game overloads you with a massive list of equipment, even early on, and it's just overwhelming to me. I had a similar feeling for the rest of the game's mechanics. I like how there's bigger job variety but I just couldn't get over how to progress my characters and it's remained a game I just walked away from. Maybe I'll pick it up again after I finish my current, comprehensive, Lawful second playthrough of Tactics Ogre, but at the end of the day it's a Tactics game that's not made by Matsuno and that's like playing a Metal Gear game that's not made by Kojima.