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The only thing that affects gambling is character level.

Items generated for the gamble stock are -5 through +4 levels of your character's level with a minimum item level of 5. Note, this does not apply to level requirements often seen on items also known as required level. This applies only to the item level. This item level is never seen by the player in game and is used primarily in formulae that choose what affixes an item can get. Ancient armor has a quality level of 40, which means you can see it in the gambling screen at level 35. You will see it more often in the gambling screen when you are level 44 because at this point, you will always meet the required level. Look at the bottom of this page for a list of base items and their proper quality levels.

Chance to gamble:
Uniques 1 in 2,000 (0.05%)
Sets 1 in 1,000 (0.10%)
Rares 1 in 10 (10%).
Magic Items are 1/~1.1 (89.85%).

Chance to get exceptional item:
Probability = max{0%, (ilvl - qlvl) * 0.9% + 1%}

ilvl = clvl (-5 to +4)
qlvl = quality level of item

Gambling +2 skill amulets

The +2 skill modifier on an amulet has an ilvl of 90.

Characters can start gambling +2 skill amulets at level 86. There is a 10% chance to gamble an amulet with sufficient ilvl that can have +2 skills. To put it another way, at level 87 there is a 20% chance that an amulet can even have the possibility of +2 skills.

Lvl Chance
86  10
87  20
88  30
89  40
90  50
91  60
92  70
93  80
94  90
95  100
Characters 95 and above will always gamble an amulet with an ilvl sufficient for +2 skill prefixes.

Gambling Tri-res rings.
Triple resist rings with resistance to fire, cold, and lightning... And maybe 10 FCR (faster cast rate).

10 FCR alvl=5
21-30 FR/CR/LR alvl=18

Level 23 would be an appropriate level to attempt gambling tri-res rings.

Gambling dual-leech rings

3-4% life leech alvl=14
5-6% life leech alvl=47
2-3% mana leech alvl=25
4-5% mana leech alvl=58

If you desire a low-end dual leech ring, gamble at level 30. There is the possibility of gambling a tri-res rings .
For a high-end dual-leech rings, gamble at level 63.