Last night at our FLGS (where I recently started running a Swords & Wizardry Light Campaign) we had an interested spectator who wanted to be a player.
"Can I convert my 5e Halfling Cleric to Swords & Wizardry?"
It was then pointed out to me that BtB, there are no Halfling Cleric PCs in SWL. I know, I wrote the rules. There also aren't Dwarven Clerics and the party already had one of those.
Give me a backstory that explains how and why you want to "break the rules as written" and its quite likely I'll go along with it. At the very least, I'll explain my rational for saying no if that's the case.
Gaming is as much about empowering the players as it about the actually game rules. Actually, empowering the players is probably the key to everyone having fun. I don't mean empowering by making their PCs more powerful but by allowing them to invest themselves into the campaign, because without player buy in you really don't have much of a campaign. So, most likely Yes to that class / race combo that isn't allowed by the book, but you better make an effort to sell me on it.
You want to try what? A running power leap into the door with strange metal swirly things and you're a halfling with 8 strength? Sure, roll a d20 and roll under strength. You have a penalty of 4 due to your size. 20? Great - you do that Wylie Coyote deal - you hit the door with a thump and hang there for a second before sliding to the floor.
Yes can lead to fun situations. No just leads to disappointment.
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