Might I suggest that you're playing with too small a band of DMs? While I have encountered these people - I do not play in their games long. My approach has been:
This has been "any DM I could find online that offered a game that sounded even remotely like what I might enjoy." Well, that would accept my application, anyway.
1.) Make suggestions.
2.) Demo the suggestions by offering to run a one shot and asking them to give me feedback on what they liked.
3.) Encouraging them when they try the things I suggested.
If those steps fail, or I am cut off from being able to take the next step, I don't tend to play in their games (where the issue is serious). I've played long campaigns with scores of DMs over the years. I've walked away from far more tables.
I would never run 5e by choice, so #2 is out, and even if it weren't, there's genuinely probability 0 that any of the aforementioned DMs would assent to joining the proposed one-shot to demo anything. Finally, #3 is impossible, as that would require that they actually try anything I suggested in order to then encourage them for doing so.
Essentially every time, I've not needed to walk away. The game has folded before any bright lines were crossed. After like the fifth or sixth completely unrelated DM who was either blithely dismissive or actively hostile to any suggestions or efforts at discussion (like "is it possible that we could start at a higher level? In my experience, level 1 is extremely fragile" or "It feels like skills are really limited, could we talk about ways to make them more useful?"), I gave up trying. If one out of seven DMs actually listens to me, then my time is better spent figuring out how to enjoy what game I can get, rather than wasting my time talking to a brick wall.
Anyway, now that my view of the thread isn’t so cluttered…
@EzekielRaiden Can you restate briefly where you’re at with the subclass? I am interested in your thoughts here.
For context, I loved the 4e assassin so much that I spent hundreds of hours on the wotc boards figuring out the most elegant solutions to its shortcomings without changing its nature. Executioner bypassed a lot of issues and ran great with the feat or whatever to use shrouds instead of the normal executioner damage boost.
My assassin class can force a dex save on an enemy as a reaction to rolling initiative, to swap places in initiative with that creature, and can place a shroud as part of rolling initiative.
Subclasses will have different round one ambush type stuff, but the base class sets up very fast strikes as well as the “move kill move” feel that assassins should have.
What would you do if you have to rewrite the phb assassin rogue?
I do not recall actually saying I would re-design the Assassin subclass, but I'll give it a look. Currently doing dinner stuff and then working to onboard a new player for my DW game, so I won't really be able to do it right away. But I might have time later, new player goes to bed earlier than I do (time zone differences.)
But as a preliminary thing, I would probably either:
1. rewrite the level 3 bonus so that it is less dependent on favorable DMing (e.g. maybe instead of damage bonuses only on surprise rounds, it could be an ability to "shroud" yourself, allowing yourself to hide in plain sight and get bonuses when attacking while Shrouded, but this ends the Shroud on you)
2. replace it entirely with some kind of poison-related feature, since assassins are strongly linked to poisons
And then also offer unique/distinctive fighting styles that reference various real-world "assassin"-type things, e.g.
kusarigama, hidden weapons, kunai-throwing, maybe some kind of poison thing (whether or not option #2 above is in place).