Inquisitive archetype Rouge multiclassing as a Way of Shadow Monk. What should the leveling path be? What magic items/feats would best compliment his abilities? Noble/Spy/Knight background? What is/are your favorite Batman Quote(s)? What race would best compliment theme/stats?
My current idea is to level him as a rouge till level 3, level him as a monk until level 6, continue rogue until level 9, and finish with full levels in monk.
Race of Variant Human.
Background of Knight, (note: Retainer - Alfred)
Goggles of knight would likely compliment well. As well as the Alert and Fighting Initiate Feats.
I do not watch enough Batman movies, but I’m pretty sure at some point he says “I’m not wearing hockypants”.
The problem with trying to build Batman (or any superhero, really) in DnD is that the characters have existed for too long so they just are too much at the same time. You can always only try to represent a specific aspect of them. Also they'd often be way past level 20 so even if you think you come close to having created Batman keep in mind that you'll be a very very very rookie version of him regardless.
On that note, let's look at your multiclass. Normally when doing a martial multiclass you'd want to get to Extra Attack as fast as possible, however since one part is Rogue you'd be fine by ignoring that for a while and rely on Sneak Attack. So the actual question is whether you're more interested in doing skill checks or in making unarmed strikes and the stuff Way of Shadow offers. Personally I'm not a fan of multiclass builds where the Monk isn't like 80-90% of the build since not getting all those Ki points and extra abilities really hurts. Also keep in mind that your unarmed strikes don't qualify for the Rogue's Sneak Attack feature unfortunately.
To be completely honest, Rogue/Monk is not really that great as multiclass and even worse if you don't use weapons. It's mostly just the Expertise and the Inquisitive features that are of interest to you and for the Monk it'd be only the weak unarmed strikes, Extra Attack (which you could get elsewhere), stunning strike (which you can barely use with such a low amount of Ki and the Way of Shadow features (where the spells cost you a lot of Ki as well). They are already way too similar in their base design. Thematically it would be on point but mechanically I feel like it would be rather underwhelming. Overall you'd probably be happier by not going Monk at all. Unarmed strikes are weak compared to weapon attacks and not benefiting from the Rogue's Sneak Attack will lower your damage output even further. If you really want to make unarmed strikes consider putting some points into STR and getting the unarmed fighting style instead of going for Monk levels though. It would still be weak but much healthier for your overall build.
Race variant human is obvious. Nothing else would be correct and a free feat is hard to pass on. Fighting Initiate for Battle Master maneuvers or Unarmed Strike fighting Style would be the most fitting choice I'd say.
Background Knight or Noble is what I'd go for as well.
I suggest taking a look at good 'ol google. There have been people building Batman in DnD 5e for many many years already. No need to do it all over from scratch again. A selection of other subclasses fitting for Batman you could look into: Battle Master Fighter, Gloomstalker Ranger, Armorer Artificer, Vengeance Paladin
Inquisitive archetype Rouge multiclassing as a Way of Shadow Monk. What should the leveling path be? What magic items/feats would best compliment his abilities? Noble/Spy/Knight background? What is/are your favorite Batman Quote(s)? What race would best compliment theme/stats?
My current idea is to level him as a rouge till level 3, level him as a monk until level 6, continue rogue until level 9, and finish with full levels in monk.
Race of Variant Human.
Background of Knight, (note: Retainer - Alfred)
Goggles of knight would likely compliment well. As well as the Alert and Fighting Initiate Feats.
I do not watch enough Batman movies, but I’m pretty sure at some point he says “I’m not wearing hockypants”.
The problem with trying to build Batman (or any superhero, really) in DnD is that the characters have existed for too long so they just are too much at the same time. You can always only try to represent a specific aspect of them. Also they'd often be way past level 20 so even if you think you come close to having created Batman keep in mind that you'll be a very very very rookie version of him regardless.
On that note, let's look at your multiclass. Normally when doing a martial multiclass you'd want to get to Extra Attack as fast as possible, however since one part is Rogue you'd be fine by ignoring that for a while and rely on Sneak Attack. So the actual question is whether you're more interested in doing skill checks or in making unarmed strikes and the stuff Way of Shadow offers. Personally I'm not a fan of multiclass builds where the Monk isn't like 80-90% of the build since not getting all those Ki points and extra abilities really hurts. Also keep in mind that your unarmed strikes don't qualify for the Rogue's Sneak Attack feature unfortunately.
To be completely honest, Rogue/Monk is not really that great as multiclass and even worse if you don't use weapons. It's mostly just the Expertise and the Inquisitive features that are of interest to you and for the Monk it'd be only the weak unarmed strikes, Extra Attack (which you could get elsewhere), stunning strike (which you can barely use with such a low amount of Ki and the Way of Shadow features (where the spells cost you a lot of Ki as well). They are already way too similar in their base design. Thematically it would be on point but mechanically I feel like it would be rather underwhelming. Overall you'd probably be happier by not going Monk at all. Unarmed strikes are weak compared to weapon attacks and not benefiting from the Rogue's Sneak Attack will lower your damage output even further. If you really want to make unarmed strikes consider putting some points into STR and getting the unarmed fighting style instead of going for Monk levels though. It would still be weak but much healthier for your overall build.
Race variant human is obvious. Nothing else would be correct and a free feat is hard to pass on. Fighting Initiate for Battle Master maneuvers or Unarmed Strike fighting Style would be the most fitting choice I'd say.
Background Knight or Noble is what I'd go for as well.
I suggest taking a look at good 'ol google. There have been people building Batman in DnD 5e for many many years already. No need to do it all over from scratch again. A selection of other subclasses fitting for Batman you could look into: Battle Master Fighter, Gloomstalker Ranger, Armorer Artificer, Vengeance Paladin
I've never encountered a forum where I got this many "talking to a wall" impressions as this one...