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Message: <blockquote data-quote="Fenris-77" data-source="post: 7619576" data-attributes="member: 6993955">If you want to maximize the number of ones you reroll, you need to maximize the number of dice you roll. Seems like some Captain Obvious stuff, but that's the place to start. The best way to roll the maximum number of d20s in combat is to maximize attacks and maximize the potential for advantage. If you want to (mostly) cap the discussion around 12th level you have a lot of room when it comes to base attacks. Only the fighter gets more than one extra, and then only at 11th level, so not a lot of room to dip for synergy. There are lots of options for the base second attack though, so lots of room to play.One solid option is to dip Ranger 3 and go Gloomstalker for the extra attack in each first round of combat (with the extra d8 damage). If you combine that with Monk and go way of the Shadow you are going to end up with a halfling ninja, which would be friggin' awesome. One the first round of combat you're rocking three monk weapon attacks and three unarmed strikes (Flurry of Blows). Shadow Step lets you manufacture advantage on your first attack, which you use for Stunning Stike, which, if it works, gets you advantage on all your other attacks that turn. Fun.If you were going to go GloomStalker 3/Monk 9 you might still want to consider archery style, as you can throw monk weapons so long as they have that key word. So daggers mostly, but it's still not useless (call 'em ninja stars if it makes you feel better). Going SS for a feat can still be pretty deadly with thrown weapons, so that's an option.The other option that works ok there for this MC is Dueling Style to get +2 dmg on all your monk weapon attacks. You will also be making a ton of Stealth rolls with this character, which gives you yet more opportunities for Lucky to kick in.Another version of the same idea is to go Assassin 3/Monk X for the first round advantage and crits. I find the Gloomstalker build a little more reliable encounter to encounter, but the Assassin build is better nova if you're building that way. Ideally, at that point, you're looking at Fighter 2/Assassin 3/Monk 6-7 and you're playing with a ton of attacks and crits.</blockquote>

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