I've had characters up to about 53 in Oblivion, when they maxed out all their major skills. I tend to cap them around 26-27 with unused majors these days, as that allows all possible creatures up to Lich to appear. Higher levels don't change the game much beyond making Goblin Warlords take forever to kill. Despite the usual criticism of the Oblivion level system, it's quite amenable to player control.
Skyrim characters haven't reached their peaks yet, so too soon to report. Only Fleur is likely to keep going, the others were rolled for testing. Perks in specific skills seem to be more important than overall level, which has few apparent effects. In particular, it appears to be possible to hit the same defence cap with any armour if you boost your Smithing skill enough. Leather (much improved) > Daedric (base level)! It appears the same is true for weapons, and a well-honed steel axe will do more damage than a fearsome-looking daedric one, too. I haven't figured out what the enemy levels do, but I suspect they cap, and the game will plateau.
Daggerfall characters didn't go past about 20. At that point they'd done all the MQ, and most of the non-random others. Player level doesn't seem to change the game much here, either. Armour/weapons at top level are available to any level of player if they find them, and that makes more difference than skill, which soon catches up. Higher levels make better loot likely, so it's not all flat, but you get to the plateau fast.
Morrowind - my first character (on my new laptop) hasn't had his first level-up yet! He may get wiped if I install a new OS to replace win 8.
Arena was just too frustrating to play for long. Extrapolating from Daggerfall backwards, I get the impression that it would get easier as you progress to higher levels, or get better equipment.
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Mods for The Elder Scrolls single-player games, and I play ESO.
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