Topic title covers it, but more specifically: say I was OCD enough to not waste a single skill point, and ended up at level 53, with all attributes at 100 and 5 major skill points to spare. Furthermore, let's say that I did this entirely legit: no training, no free skill boosts, nothing but good old-fashioned grinding. Now assume I've taken advantage of the Personality-damaging effect of the Scales of Pitiless Justice along with some of the free skill boosts to advance further. If I was to gain any more levels beyond that, is felldew addiction and its attribute damaging withdrawal effects really the only possible way to advance further? Will inflicting normal Damage Attribute statuses on myself not work? I know an extra level or two at such a point is meaningless in any strategic sense, but I'm wondering exactly what the maximum possible level one can legitimately obtain is, if one was to game the system as much as possible without actually cheating.

I think they say 255 or so is top level but you′d really only give monsters more HP. I also think you can damage or drain your attributes and major skills via self-made spells and potions and work them up again, thus advancing. Others can be more helpful here than me but it goes along something like that.

Those ways you described... and also going to jail. When you get out of jail, random skills get dropped. I don't understand why you want to do this though, level 30 is the top level for awards in the game. I've had characters who got to the end of their natural leveling, ranging from 46th to 50th level.

No way would I be able to actually do this without just using the console. This is only a hypothetical. It's more about pushing one's stats to the limit than anything practical.

Also, regarding jail, how can that increase your level if your attributes are already 100? It only drops skills. Unless you're talking about using it in conjunction with felldew addiction.

When those skills drop, you can retrain them. And then the skill "bumps" up. You are basically adding a level (or several) between now and your last level. It's just a very tedious and long process, though some have used it.

I think jail only drops partly gained skill points. Like if you are at 50 in Smithing having just gotten there and have done no more smithing but go to jail, you don't lose anything. Let's say you did some smithing after you got to LvL50 taking you 10% to LvL 51. If you go to jail, you lose that 10% to LvL 51 but do not drop back to LvL 49.

This is the Oblivion forum, not the Skyrim forum. Jail did drop earned skill points in Oblivion, letting you raise it again to level up again.

But I'm saying that, if the attributes are all 100, it won't matter how many major skill points you get. You'll just get the "perfection cannot be improved upon" message when you try to level up.

All I can think of is to try reducing your attributes, then level up and see. Perhaps a drain attribute spell. Perhaps some of these unique items - if you look, you will see many of them drain one or two attributes while equipped: http://www.uesp.net/wiki/Oblivion:Unique_Items

hehe you just made me burst out laughing, i could just imagine you sitting there with your eyes narrowed saying that coldly