Multiple characters or 1 guy for everything?

I have been playing the oblivion remaster almost every day since, release. I have made a Sword and board imperial who wears heavy armor. I have mastered heavy armor, blade and block already, not to mention mercantile, and I am an unstoppable monster, with every house in the game, 300000 Septims, and have more potions than a stomach den. I am about to finish main quest, and closed a bunch of Oblivion gates, and now thinking do I keep playing the same character and do all the guilds? Or do I make 1 character per guild, and flesh out the world with multiple characters?