I played Daggerfall for my first time when i was a kid and i stop immediately after i saw and hear the skeleton before the stairs in the first dungeon.

Nonetheless i finished it three years ago when i was 26 and the pixelated skeleton wasn't (that) frightening any more.

I'm still playing Morrowind and Skyrim extensively but the only game that i haven't finished is Oblivion.

The question is can i enjoy Oblivion without having to min max my skills for the +5 skill increase or i will be punished later in the game?

In Morrowind i just playing the game, i let my skills grow organically and i don't give a damn for the multipliers. If i hit any x4 or x5 good for me but i never go out of my way to hunt for multipliers and the game it's totally playable and enjoyable.

Can i play Oblivion with the same mentality?

I really want to delve and dissect the world but i know i will not enjoy any form of multiplier hunting.

If that troubles you just lower the difficulty. I'm usually one of those masochistic players where everything has to be as hard as possible, but with Oblivion I had moments where I burned out, created a new character and just dragged the difficulty on the left side of the bar.