Thanks for replying everyone, I am beginning to grasp how this works.
If you don't mind, here is another example.
(Keep in mind that Perks/Skills/Potions are the same. This helps me understand a bit better instead of having to factor in all these extras)
Suppose I find an Ebony bow when I reach level 30. I upgrade it when I reach Level 40, Level 50, Level 60. (just using this for a scenario, I realize it may not be correct.) After these three upgrades the Bow now has Legendary status.
While at Level 60, I find another Ebony bow. I upgrade it ONCE and it reaches Legendary status after only one upgrade.
My question is will the two bows have the same stats? Remember no potions/skills/perks factored in. (While it may be impossible to do it without these, this is just a "what if" type question so please bear with me.)