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Okay, this is pure theory crafting and I do NOT intend to play this character, it's just something a buddy and I came up with last night, and I wanted to know if it would work AT ALL.
So the idea would be a rogue dock worker type with ranks in profession (dock worker) or (construction worker) and the rough and ready trait with a crowbar (for the +1 to hit). Level 1 (human) he gets combat expertise and catch off guard. Level 2 he picks up improved disarm with the combat trick rogue talent. Then, whenever he fights a standard (non monk, non brawler) humanoid without natural attacks, he walks up to them, disarms them, then beats face with the crowbar (for sneak attack damage).
Thing is, can he enchant his crowbar? I realize that he won't always be able to pull this off, and he'll need a magic weapon eventually so he can hit things that have dr/magic or ghosts or whatever. The 'trusty buddy' (an adamantine crowbar you can get from a scenereo) still gives you the -4 improvised weapon penalty, so I assume it's not 'masterwork' and cannot be enchanted as a weapon. Is there a PFS legal way around this? What If I masterwork transformation a crowbar? Can it be enchanted as a weapon then? Is so, does that stop it from being an improvised weapon?

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It is reasonable to think you could do all these things, in a home game.
But the Rules don't explore whether you can make an "improvised weapon" into a magical weapon.
Since the rules are absent on this, you will get a huge amount of table variation in PFS. And if you base your entire build on something that will have lots of table variation, you may find your character useless in some adventures.
I do admit, the thought of such a character is a fun one.
Perhaps just carrying around oils of magic weapon or bless weapon will be enough?

JT$ |

If it's adamantine, it's already masterwork. The issue is whether it's a named item or not, you can't upgrade named items. I would say it is, because of the +4 circumstance bonus to STR checks, that is a unique quality of Trusty Buddy not factored into the price.
I think you could just buy an adamantine crowbar for 3002gp and upgrade it. It would just have the normal +2 to STR checks.

PolydactylPolymath |

Oils of Bless Weapon will go a long way, as will the Improvised Weapon Mastery feat (eventually). Greater Magic Weapon will work also--your best bet here is to carry around a scroll and a Mnemonic Vestment to lend to any spontaneous caster.
From what I understand about Trusty Buddy, it's worded in such a away that it overcomes ALL DR, not just DR/Adamantine. I'm not sure if this was ever addressed or clarified, however.
EDIT: The Wildcat and Monk of the Empty Hand monk archetypes both confer additional prowess with improvised weapons, and from what I can tell, both are compatible. Something to consider for multiclassing.

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There's a long-stading question about whether a "masterwork tool" only gives the +2 to its tool-like uses, or is also +1 to hit, if you swing it at someone. (So a "masterwork shovel" gives you a +2 skill roll for, like, craft (ditch), but does it also give you a bonus if you attack someone with it as an improvised weapon?)
That's the issue with making masterwork tools into magic weapons. Some GMs are fine with it, and others don't allow it.

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If it's adamantine, it's already masterwork. The issue is whether it's a named item or not, you can't upgrade named items. I would say it is, because of the +4 circumstance bonus to STR checks, that is a unique quality of Trusty Buddy not factored into the price.
I think you could just buy an adamantine crowbar for 3002gp and upgrade it. It would just have the normal +2 to STR checks.
It would be as much a named item as a Mithral Shirt. Which can be upgraded.

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Glamered
Price +4,000 gp
Aura moderate illusion; CL 10th; Weight —
DESCRIPTION
A glamered weapon can be commanded to change its shape and appearance to assume the form of another object of similar size. The weapon retains all its properties (including weight) when so disguised but does not radiate magic. Only true seeing or similar magic reveals the true nature of a glamered weapon while it is disguised. After a glamered weapon is used to attack, this special ability is suppressed for 1 minute.
CONSTRUCTION REQUIREMENTS
Craft Magic Arms and Armor, disguise self, magic aura; Cost +2,000 gp
You can use a regular crowbar, and once you can afford that get a real weapon. I would not try to keep the improved weapon thing after a certain level. Once you fight certain creatures something like this just seems quaint... also get a backup alchemical silver and cold iron crowbar^^

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It has to be an improvised weapon in order to get Sneak Attack damage with Catch Off-Guard.
Thank you, I never really took a good luck at that feat. Now that I have done so: the feat is bananas, since it allows you to sneak attack a dragon, just because the guy charging towards it ( with magic armor and items obviously) carries a crowbar, instead of a mace.....
Suuuure. Sorry but that is really not my cup of tea, good luck.

Pirate Rob |

“Armed” Unarmed Attacks: Sometimes a character's or creature's unarmed attack counts as an armed attack. A monk, a character with the Improved Unarmed Strike feat, a spellcaster delivering a touch attack spell, and a creature with natural physical weapons all count as being armed (see natural attacks).
I don't believe creatures with natural attacks are "unarmed."

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CRB wrote:“Armed” Unarmed Attacks: Sometimes a character's or creature's unarmed attack counts as an armed attack. A monk, a character with the Improved Unarmed Strike feat, a spellcaster delivering a touch attack spell, and a creature with natural physical weapons all count as being armed (see natural attacks).I don't believe creatures with natural attacks are "unarmed."
I learn something new about the CRB every day^^, yeah it that case it doesn't seem quite as broken, but scaling seems to be a problem.
Still not my cup of tea though, so I will quietly withdraw, before I make another blunder.