Ha, a couple of us here spent this very morning crunching the numbers that you are asking about by testing in-game.
The short version is that in order to reach "Legendary" upgrades without +Smithing enchanted gear and potions, you will need a weapon/armor that is affected by a smithing perk (that you have spent points in), i.e., steel, elven, dwarven, glass, ebony, daedric. The minimum required Smithing skill to do this is 91 for any type of weapon/armor. If you are trying to reach Legendary status with any other type of upgradeable material, you will need a Smithing skill of 168 or higher, which is obviously going to require some enchants/potions to get to.
Notes:
Once you reach a point where you are crafting legendary gear, it takes about 17 skillpoints more to reach the next "level" of legendary where you will see a boost in damage or protection. Although there is an armor cap of 80% that is reached by having an AR of 567 or higher, there is no realistic limit on weapon upgrades... in other words, there's basically hundreds of higher levels of "Legendary" that you can craft by using game exploits like the restoration potion glitch. I saw a youtube vid some guy made after abusing the resto loop where he was walking around with a sword that did IIRC over 25,000 damage per hit -- I guess that was a TES version of the lightsaber or something.
