I think “fiddly” was a fair thing to say about how you first presented the equipment… having boots give you a bonus but get ruined if worn in terrain A, B, or C… so you must bring a different pair of footwear on adventures… or oil that helps reduce the encumbrance for the purposes of proficiency throws for skill X (but not throws for skill Y also tied to encumbrance).
I like this equipment list better. For the record, I have no problems with using equipment to let thieves do their job… what would a fighter be without armor and weapons after all? (probably dead.)
I almost… almost… want to say just add one piece of equipment:
Thieves’ Kit: A thief’s kit includes everything a thief needs to do his job. It consists of a set of lock picks and files, a pair of padded boots, a couple patterned cloaks for camouflage, an ear funnel, discrete climbing gear, blackener paste, and special straps and harnesses for securing equipment. A thieves’ kit can only be employed when wearing leather armor or less. When in possession of a thieves’ kit, a character gains a +2 bonus to proficiency throws to perform thief skills.
… but that’s probably not a very satisfying solution
Here’s my critique of the equipment list and using equipment as a “fix”:
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I’m glad to see knotted rope go. When you use a rope to climb, it just works.
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Weapon/Armament Blackener is pretty cool. I don’t think you need any concrete game mechanic tied to it. It’s kind of on the level of a blanket. I’d keep it. Imaginative players will find good uses for it and what self-respecting assassin doesn’t want their weapons blackened?
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Ear Trumpet. I like this item. It doesn’t meaningfully help the thief though. The thief already has a decent chance at succeeding at this and everyone can attempt to Hear Noise with some classes being equal to a 1st level thief in ability. In practice, this is one of those skills that often succeeds through redundancy as several people make an attempt at the same task.
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Padded Shoes. I like this item. With respect to verisimilitude, I’m wondering if padded shoes are better than bare feet (i.e. young Conan) or moccasins? Aside from that, the fire damage thing seems contrived, I don’t think that’s necessary. Instead of being destroyed if immersed in water, I’d say they don’t work when wet.
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Thieves’ Garb. Very Nice!
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Superior Thieves Tools. Their cost won’t help 1st level thieves who need it most.
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Masterwork Thieves Tools: Their cost won’t help thieves until about 3rd level.
I know I’m probably coming across as overly critical, but honestly I do like the potential of this route. I definitely want to dwell on it a bit more.