I just recently got hook into smithing so I went and tried to improve my wolf armor chest to flawless and I only did it once so can I do it again or that's it cause it doesn't let me do it the second time? And if is that's it, does that also apply to every other piece of armor equipment, for example the Daedra armor sets?

Five times: Fine, Superior, Flawless, Epic, Legendary.

You can keep upgrading as long as you have the materials.

You can improve it as many times as you want. If the armor is greyed out, it's because you haven't raised your smithing skill enough to make it better.

I see cause my smithing skill as of now on my level 15 is only in the 50's but how come is only took me once to went from fine to flawless? Does it go in order or it is just random?

It depends purely on your skill value. For example, you only have to improve an item once to make it Legendary, if your smithing is high enough (91).
You can see the breakpoints http://www.uesp.net/wiki/Skyrim:Smithing#Item_Quality.

Enchanting or Alchemy gets it even higher if you want.

Unlike what you may be used to in MMORPG, you actually cannot "stack" upgrades. Each upgrade, if it is of higher magnitude, replaces the old upgrades. You can upgrade any number of times but it wouldn't do you much good except wasting your materials.

The grading actually distracts you. There is a range for each grade and the legendary grade, being the last grade is very very wide. It is altogether possible that someone's legendary blade has twice the damage of your legendary blade.

The upgrade magnitude is dependent on your smithing skill, smithing perks, fortify smithing bonus on your equipment and fortify smithing bonus from potions. The strongest bonus is 100 smith skill, double upgrade bonus from relevant perk, four pieces of +29% fortify smithing equipment and a +130% fortify smithing potion.

You automatically improve to the highest condition you are capable of improving an armor piece. (Oh, and I was wrong, its actually six ranks: Fine, Superior, Exquisite, Flawless, Epic, Legendary). How high you can improve is dependent on your Smithing skill. Perks cut the needed skill for certain armors in half (well, almost).

The levels are (in parentheses are the ranks with perks)-

Fine - Always
Superior - 31 (22)
Exquisite - 65 (40)
Flawless - 100 (57)
Epic - 134 (74)
Legendary - 165 (91)

Even if your armor is legendary, you can increase your smithing skill beyond 100 with enchantments, if you want. But that kinda makes the game too easy for some.