GLOG Class: Jack
You are a handyman, a dilettante, a scoundrel. Here and There are your hideouts, This and That are your tools. You have been called Jack the Lad and Jack the Ass. In the dungeon, you're Jack O' Lanterns, lighting the way.
You've just one maxim: don't end up Jack in the Box.
Starting Equipment: a two-slot unlabeled package worth up 3d6 gp, a list of names, a dagger, tools of a craftsman's trade.
For each template of Jack you have, get +1 Stealth.
A: Master of None, Always Prepared
B: Be Nimble, Be Quick
C: Jackpot
D: Jack of All Trades, Giantslayer
Master of None
Whenever you encounter a task that the GM determines requires the use of a particular skill, you may roll [Jack templates]-in-6. If you succeed, you know what is relevant to that situation as if you had that skill. This only applies to that check or task. Rolling and knowing how to pick one lock or know one historical fact does not grant the ability to crack other locks or a general history knowledge. It also does not grant automatic success unless having the skill would be sufficient to succeed.
Always Prepared
In town, you may spend any amount of money to buy an Unlabeled Package. When the package is unwrapped, you declare what it contains, as long as the contents comprise the appropriate number of Inventory Slots, don’t cost more than you originally paid, and are available in town. You can put multiple items inside a large Unlabeled Package, including smaller Unlabeled Packages. You can have up to two Unlabeled Packages at a time.
Be Nimble
On each of your turns, you may take an extra action. This action cannot be used to deal damage (directly) or cast a spell (directly).
Be Quick
You have +[Jack templates] to initiative checks and movement.
Jackpot
You may always choose to reroll a failed roll, as long as it wasn’t a Jackpot reroll. If you succeed on the roll, you cannot use Jackpot again until you next rest.
Jack of All Trades
You are proficient in the use of anything you revealed from one of your packages. Your packages are twice as efficient as regular storage, meaning that you could for instance, store a two slot great sword in a one slot package. You can have up to four unlabeled packages at a time, and you can restock them overnight by spending the appropriate money even if not in a town. Restocking out of town cannot include perishable items.
Giantslayer
When you attack an enemy, list off every distinct advantage they have over you that you can clearly identify. For each such advantage, you deal +1 damage on attacks against that enemy until the end of the fight. You may name new advantages as they appear for extra +1s.
(Ex: an ogre mage is bigger, stronger, tougher, and can cast magic)
Differences that are redundant or irrelevant to the situation should be ignored (sex difference, claws when you have your own weapon, the ability to spider climb when you’re in the open, etc.).
Design Notes
GLOG challenge 3: Design a class for a player in one of your games. His favorite class so far was sorcerer, which felt like a very open-ended prompt - what can’t a GLOG sorcerer do? (Hint: it’s damage)
Sorcerers are all about supreme flexibility in creating their own power, as well as not running out of gas. Rather than trying to recreate an open-ended caster, I decided that a mundane version was more appealing, and started looking for analogues.
I settled on the Thief. Unlabeled Packages, in particular, allowed for the nearest version of spontaneous ready-for-anything spice. A variant Thief would do quite nicely. Always Prepared is probably the most flexible "mundane" feature I've seen, so building on it just made sense. Opportunity for action is the name of the game - Be Nimble incentivizes creative action, Be Quick helps you get in position on schedule, Always Prepared provides tools, and Jackpot lets you gamble on hail-Marys without the "wasted re-roll" feeling you get from the Thief's Lucky - something I've seen a lot of from my fellow party member in my own GLOG campaign.
The player in question read the class and said I was spot on with my assessment of how to cater to his play preferences and could actually imagine playing this class, which pleases me.