With Crossbow Expert feat - can you Bonus Action attack on your turn, and then use a readied action to attack on someone else's turn?

Question

I am playing a crossbow expert ranged rogue and trying to maximize my sneak attack capabilities in order to remain competitive with regard to DPR (Paladin and Fighter in the group).

I am wondering if by RAW, I can use the bonus action attack provided by this feat first and then if it is successful, ready my regular attack to trigger on someone else's turn - essentially allowing me a chance at two sneak attacks within the round.

I am solo-classed, so I don't have access to Extra attack and not looking to abuse Haste. I am wondering if this is in DM-rule territory or if there is some source I can point to that would allow something like this?

Answer 1

If you are readying an action you aren't taking the Attack action

In order to take the bonus action attack of Crossbow Expert you have to take the Attack action (emphasis added):

When you use the Attack action and attack with a one-handed weapon, you can use a bonus action to attack with a hand crossbow you are holding.

— Player's Handbook, p. 165

The Attack action (PHB 192) let's you take an attack on your turn, while the action which lets you take an action on another turn (as a reaction) is the Ready action (PHB 193). If you are taking the Ready action you aren't taking the Attack action on your turn (which is when you can take bonus actions) and thus can't take the Crossbow Experts bonus action.

Answer 2

Only if you have two Actions available and use one to take the Attack action.

In order to benefit from the Crossbow Expert feat, you need to be taking the Attack Action, but in order for you to ready an action, you need to take the Ready Action. As a result, if you want to do both, you're going to need to have two Actions available to use on your turn.

The two most notable examples of this would be if you're either a Fighter using the Action Surge ability or you're under the effects of the haste spell.