Hmm... is the ' –4 penalty to all charisma checks and charisma-based skill checks' deliberate? With only three Ugly Strikes per day, the wearer will never 'break even' in this case. Is it your intention to impose a minimum -1 penalty?
Also, 'ability damage' has specific meaning in D&D 3rd ed... I really do suggest re-terming it as a penalty. (Basically, all damage stacks and do not 'go away', in the sense that hp damage does not 'go away'. The damage is done, the magic over. All you can do is heal the damage, either naturally or with magic.)
BTW, on the issue of pricing:
I would price this as a cursed empowered ray of enfeeblement effect, CL 5, 3/day.
The ability to penalize Dex, Con, etc. at you choice instead of strength only is obviously better than Str only (especially Con!), but 2 points per attack, maximum, is definitely worse than the (1d6+5)*1.5 = 9 ~ 15 per hit for an Empowered RoE. Furthurmore, the Ugly Strike requires a touch attack to deliver -- a tricky thing, sometimes: especially against the likes of a purple worm.
Empowered Ray of Enfeeblement effect, CL 5, 3/day:
3 SpLvl x 5 CL x 1800 x (3 / 5) = 16200
As for the curse, the -3 penalty to all Charisma-checks and Cha-based skills, I'd just take the price of a +3 bonus to all Charisma-checks and Cha-based skills out of the price of the cloak. Luckily, we have an item Circlet of persuasion (4500 gp), that grants exactly that +3 bonus. Its even CL 5. How nice!
So our price for the cloak is 16200 - 4500 = 11700 gp
Personally, I find 11700 gp a bit expensive for such an item. I would probably DM fiat a 75% discount for the EmpRoE effect. Call it a price reduction due to reducing a ray effect to touch range.
16200 x 75% - 4500 = 12150 - 4500 = 7650 gp, which I think is in the ball-park.
A 7650 gp cloak could be worn by a 7th level PC (40% total wealth) or a 10th level NPC (47% gear value), which is about right for a 'boss' type encounter. If you want it to be cheaper, a 50% discount for the EmpRoE effect will get you:
16200 x 50% - 4500 = 8100 - 4500 = 3600 gp, compairable to a +2 Cloak of Resistance
3600 gp is 40% of the wealth of a 5th level PC, and 38% of the gear value of a 8th level NPC character, so you may introduce the cloak at about party-level 5 in this case.
So in the end we have:
Cloak of Ugliness
(descriptive text)
Moderate necromancy; CL 5th; ray of enfeeblement; Price 11700 gp, 7650 gp, or 3600 gp; Weight 1 lb.
Hope you find this useful! I certainly had fun!
Also, 'ability damage' has specific meaning in D&D 3rd ed... I really do suggest re-terming it as a penalty. (Basically, all damage stacks and do not 'go away', in the sense that hp damage does not 'go away'. The damage is done, the magic over. All you can do is heal the damage, either naturally or with magic.)
BTW, on the issue of pricing:
I would price this as a cursed empowered ray of enfeeblement effect, CL 5, 3/day.
The ability to penalize Dex, Con, etc. at you choice instead of strength only is obviously better than Str only (especially Con!), but 2 points per attack, maximum, is definitely worse than the (1d6+5)*1.5 = 9 ~ 15 per hit for an Empowered RoE. Furthurmore, the Ugly Strike requires a touch attack to deliver -- a tricky thing, sometimes: especially against the likes of a purple worm.
Empowered Ray of Enfeeblement effect, CL 5, 3/day:
3 SpLvl x 5 CL x 1800 x (3 / 5) = 16200
As for the curse, the -3 penalty to all Charisma-checks and Cha-based skills, I'd just take the price of a +3 bonus to all Charisma-checks and Cha-based skills out of the price of the cloak. Luckily, we have an item Circlet of persuasion (4500 gp), that grants exactly that +3 bonus. Its even CL 5. How nice!
So our price for the cloak is 16200 - 4500 = 11700 gp
Personally, I find 11700 gp a bit expensive for such an item. I would probably DM fiat a 75% discount for the EmpRoE effect. Call it a price reduction due to reducing a ray effect to touch range.
16200 x 75% - 4500 = 12150 - 4500 = 7650 gp, which I think is in the ball-park.
A 7650 gp cloak could be worn by a 7th level PC (40% total wealth) or a 10th level NPC (47% gear value), which is about right for a 'boss' type encounter. If you want it to be cheaper, a 50% discount for the EmpRoE effect will get you:
16200 x 50% - 4500 = 8100 - 4500 = 3600 gp, compairable to a +2 Cloak of Resistance
3600 gp is 40% of the wealth of a 5th level PC, and 38% of the gear value of a 8th level NPC character, so you may introduce the cloak at about party-level 5 in this case.
So in the end we have:
Cloak of Ugliness
(descriptive text)
Moderate necromancy; CL 5th; ray of enfeeblement; Price 11700 gp, 7650 gp, or 3600 gp; Weight 1 lb.
Hope you find this useful! I certainly had fun!

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