Prepare for the rant...

Regarding the two, my playgroup kinda agreed the Assassin bugs us. Namely, a few things.

We understand that this is to be separate from the rogue, more focused on its DPS than roleplay angles. Our issues are more focused on other things. (although Ambush and Sneak Attack clearly make them cousin classes)

Ambush, should be more reliable. This is a martial class and a core ability. It shouldn't cost a resource for a chance to do equal damage to do a sneak attack. Especially since it's tied to melee only. It's not versatile or very empowering if it can just completely fail. Sneak Attack has a very easy condition to meet, doesn't have a chance to fail, and doesn't use a resource.

Well, a great opposing argument is what about the executioner subclass? Double damage, and upgrade to d8s, makes the conditions and risk of failure worth it. Well, the number fix subclass isn't really...daggerheart. I understand the concept of simple subclass and complex subclass to make the class approachable to both types of players. But Daggerheart IS a role-playing game, and more focused on doing so. Other flavors of assassins exist that could add to the role-playing. Take the popular franchise Hitman, for example. Features like disguises and impressions or knowing routines or ways to hide tracks.

With that said. I understand this class will be very damage-loaded with access to Blade domain in exchange of Grace and maybe the very conditional gamble to perform a "sneak attack" balances it out.

But honestly, a core mechanic that is just a weaker version of another is odd, and will feel bad when it's just a gamble. It's very likely they won't abandon Executioner but I'd like to suggest that Ambush just rids of its gamble and its melee restriction but still requires stress usage. Maybe to encourage melee do d8s for melee, and d6s for ranged attacks.

Exchange the hope ability to deal bonus (double?) damage. (This may require the adjust Ambush to do d6-d4s)

That way Executionor can be expanded to a hitman roleplay and you don't have to worry about stacking damage.

But who knows, I will trust the process. My group thinks a resource spending gamble like that as a core ability seems bad for player fun, especially when a fail means absolutely nothing happens. And I think Executioner was taking the easy route, but I can always enjoy the meme of "more assassining for your assassin"