Converting Skull and Shackles to 5e

[Meibolite]

Hey Fellow playgrounders,

I'm currently gearing up to run the Skull and Shackles AP from pathfinder in 5e for a group of people, and while I'm having a rather easy time converting most things, I'm having doubts as to whether or not the changes i'm making to the Traits from the player's guide for Skull and Shackles to turn them into backgrounds is going down the right path.

My main concern is for the Ships Surgeon background. I wanted to give it a bit more flavor for it's feature, than just "you have advantage on Wis(Medicine) checks" so I incorporated the Peg Legs & Eye Patches side bar. The background is as follows

Spoiler: Ship's Surgeon

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Ship's Surgeon
Skill Proficiencies: Medicine, Survival
Tool Proficiencies: Carpenter's Kit, Medicine Kit
Feature: Makeshift Surgery
When you make a Wis(Medicine) check to stabilize a character and you fail, you may re-roll with advantage, if you succeed, the patient stabilizes, but loses a limb or gains scar. Roll one more time to determine the injury on a d20. See Table

D20 Injury-- Effect
1-5 Minor Scar-- Interesting but cosmetic, no changes

6-8 Moderate Scar-- Cut on face, advantage on Cha(Intimidation) or Cha(Diplomacy) checks

9-10 Major Scar – Severe cut on face, disadvantage on Cha(Intimidation) or Cha(Diplomacy) checks

11-14 Loss of Finger-- Once 3 or more fingers have been lost, disadvantage on all Dex based skill checks

15-16 Impressive Wound-- -1 HP per level at the time of injury, as if character suffered -2 to Con. Does not affect HP gain at later levels

17 Loss of Eye-- Disadvantage on all sight based perception checks

18 Loss of Leg-- Speed reduced to half, cannot take Dash action, Disadvantage on Dex(Acrobatics) checks

19 Loss of hand-- Cannot use Two-Handed weapons, Dual Wield, or Use a Shield and Weapon. Does not effect Spell-casting Disadvantage on all Dex based checks that involve using two hands.

20 Loss of Arm-- Cannot use Two-Handed weapons, Dual Wield, or Use a Shield and Weapon. Does not effect Spell-casting Disadvantage on all Str skill checks and Saving throws

I'm really worried about whether or not the loss of Eye/Leg/Hand/Arm are too extreme, or if the Ship's Surgeon background should have the ability to cause such detrimental problems for players. I personally feel the Reroll w/ Advantage on a failure warrants the danger since they are already proficient with Medicine, as well as the fact that it is a rather easy check for most characters to make.

What are your thoughts?

[Kryx]

I've already converted book 1 and 2 on google drive. See Skulls & Shackles converted to 5e
Plunder and Infamy
S&S 5e backgrounds
Ship Combat (I don't use this at all, actually)

Also if you just want the monster converter then http://marklenser.com/5econverter/

I created the programmatic converter recently and I need to go through my old stuff and verify the numbers before posting it publicly elsewhere.

[Meibolite]

Hey Kryx,

Thanks for the reply, and I like what you've done for the backgrounds, but none of the backgrounds you have posted do anything in the way of giving features, something that all the normal backgrounds give in the PHB, which is the real issue at hand for me. The features all have flavor and RP use, and my group is heavy on the RP aspect. And that's the main thing I wanted criticism on, the Sea Surgeon feature. But I do appreciate the help

[Kryx]

Sure, I just thought you might want to see what I had.

I did indeed skip the features.

[Meibolite]

Thanks for giving me access to the two books conversion, this is going to save me a TON of time ad-hocing the encounters and DCs. I'll probably post my backgrounds in a few, feel free to use the features if you'd like, and For the ones I didn't bother to make stuff up for, I'll probably use your stat blocks, and of course give you credit :) I'll post the link as soon as I get it posted to my docs page.

Can you give me your opinion though on the Ship's Surgeon ability? Do you think it's too good/bad or may irreversibly break the game for good or ill?

[weaseldust]

I wouldn't give a mechanical ability that affects other players' characters like that. Even if they enjoy the idea at first, they might find they feel differently when someone actually loses a hand. Moreover, most backgrounds give more background-y features, like knowing certain people or having a certain reputation.

I'd suggest giving them the ability to fit and adapt prostheses, just for flavour, but also give them something like the sailor's feature. Or perhaps something like being sought out by people going on long and dangerous voyages (by sea or otherwise).