I'm in the mood to roleplay a martial halfling. I was looking at Lucky and thinking about how I can make the most use of it. More as a fun exercise for what I could do with the character, not because I expect to come up with a DPR-king or anything like that. Lucky doesn't move the needle enough to optimize around it - unless you're doing it for the joy of playing around. Which I am.
For my actual played character I'll be going with whatever will be fun to run, but I had a bunch of thoughts about Lucky and I wanted to have a theoretical discussion with folks. Get your ideas so we can really make a halfling shine regardless if it's the exact one I play.
The follows is me sharing a bit of my journey of discovery, and I hope your comments lead me to unexplored territory I hadn't considered.
So, let's set a foundation: Point buy, official books only, can't rely of getting specific magic items, played levels 1-12. We can talk up to 20 but who knows if a campaign will really reach there.
That last part is a bit telling. You see, my original thought was that the best way to make use of lucky was the most attack roles. Both fighter and warlock's Eldritch Blast can manage 4 without a bonus action. But ... at the levels likely to be played the best they can do is get 3 attacks (without a bonus action) and even there most other martial classes keep up with them until 11th, which is the last 10%-ish of play. So maybe that's not as big of a deal if it's only for a bit of play.
Halfling +2 DEX talks toward finesse or ranged weapons, though +1 CHR for Lightfoot can make warlock for EB (or Hexblade I guess) reasonable.
Bonus action attacks: two weapon fighting with the fighting style is pretty accessible, and damage drop compared to finesse weapons isn't a big deal. Monk also gives a bonus action attack, with the chance to get a second for a Ki. Monk is pretty MAD though, which might take up feat space. Would have to play with it. Polearm Master gives a bigger weapon die and some other goodies, but none of the weapons (even the errata'd in Spear) are finesse, so it would have to go STR.
And really, it seems like chance to hit is big for making the most of Halfling's Lucky. The smaller the die results that miss, the bigger the boolean hit/miss effect on rerolling one of them. If you hit on a 2 you normally have a 1/20 chance to miss. But if you reroll 1s, even if you need to keep it if it's another 1, it reduces that failure to 1/400. Now hitting on a 2+ isn't likely with bounded accuracy, but it's why moving to STR would dilute the talent a noticeable amount.
Advantage is helped by lucky in a different way. It's two rolls, so two chances of Lucky coming into play. But ignoring the double 1 case, the chance that the reroll is the best roll is a little less than half (since we already know the other roll is above a 1). So it triggers twice as much but is only meaningful half as much - not that it's bad, but it's not as huge a help as it might seem on first blush.
The more I think of it though Halfling's Lucky seems to give the most bang for the buck with the smallest chance to miss - that's a big impact vs. without Lucky. Compared to that, the chance of a "standard" 65% chance to hit increasing to 68% or something seems like not that huge of a change even with four attacks a round. Though as the saying goes, Quantity has it own Quality.
If reducing chance to hit is the best case, going ranged with the Archery fighting style is attractive. Sharpshooter with its -5 dilutes Lucky even if normally it's a great feat. Crossbow Expert on the other hand adds more of that quantity. But is the opportunity cost for that worth delaying +2 DEX (which increases chance to hit and damage), or is it only worth it once DEX 20 has been achieved?
And still, could Monk be the way to go? Does two-weapon come on early enough that it's the superior choice over levels 1-12 even if it doesn't finish quite as strong? EB Warlock with Devil's Sight and Darkness? Or, more excitingly, something I haven't thought about at all?
What's your thoughts?