D&D 5E (2024) Rogue abilities help

You get the aim power being a rogue to gain advantage to attacks if you do not move. Daggers work if you need to be a melee PC given your classes in the party. This might bring in your 2-weapon bonus action things though.
 

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The Skilled feat is never a bad idea for a rogue, and only gets better at higher levels.
Sentinel is good, but at 5th level, I think you get Uncanny Dodge, which will fight for your single reaction if you're in melee and the target of attacks.
Skulker is fine: - I don't tend to need it for hiding in combat much (less useful for a Thief), but blindsight is great, not just for operating in darkness, fog etc, but also for detecting hidden/invisible opponents.

I know what you mean about Hand Crossbows, but since they don't make sense on a number of levels, I either assume that they are actually inherently magical objects, or avoid them altogether. (I feel the same about people wielding a quarterstaff in one hand and a shield in the other.)
 

It's more that I don't know, mechanically how people use two cross bows. Do you drop them? You have several loaded and ready to go??? IDK. I've never used the feat.
With the feat.
You attack once with a handcrossbow, then bonus action attack with a second one.

You can't effectively use 2 without the feat.
Once he's 5th, he'll be braver in combat. But I'm leaning hard towards this
Rule number one is to play whatever is most fun for you.

Though Skulker benefits from ranged attacks, and implies you are hidden for advantage. So I would go heavy crossbow (push) as your main weapon. Which is good for kiting and getting enemies away from wizards and into zones like Web.

And 2 scimitar (Nick) as backup.
 

With the feat.
You attack once with a handcrossbow, then bonus action attack with a second one.

You can't effectively use 2 without the feat.
But how do you reload them if both your hands are holding hand crossbows?
Rule number one is to play whatever is most fun for you.

Though Skulker benefits from ranged attacks, and implies you are hidden for advantage. So I would go heavy crossbow (push) as your main weapon. Which is good for kiting and getting enemies away from wizards and into zones like Web.

And 2 scimitar (Nick) as backup.
Hmmm. I never thought of the forced movement.
 


But how do you reload them if both your hands are holding hand crossbows
It takes special training to master the technique.

I mean, people shoot bows without any hands.
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