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I don't care what some are saying. I think this is a fabulous idea.

I like this approach. And recommend it in general, but not just for this particular character. And so my recommendation to the OP stands. Apply this to all the PCs, not just the warlock. Because to say you are not trying to single out the one player, but then singling them out in this way...

Most importantly: What are you interested in giving your PCs access to? Include that.

I will chime in with some of the others asking what it is you are looking for. What "options" are missing that would otherwise make you feel like you are playing the game you want? Maybe it doesn't look like it at first glance, but to me 5e has more breadth of options in realizing a character...

Look to the rare flame tongue and very rare frost brand. Both add bonus damage (and other benefits) and neither are "plus" weapons. Dagger of venom, dragon slayer, giant slayer, hammer of thunderbolts, and a big handful of others, that are plus weapons, are all "only" +1.

Maybe I just forgot, but what other PCs are there in the group? Any clerics or paladins? How do you normally handle their class features?

Hrm. Well. I guess the impression I'm getting is that you have a different idea of what he should be doing versus what he wants to do. And that appears to bother you enough that you feel the need to single him out for "consequences". I suggest you just tell him flat out its your game and that...

I am not opposed to this at all. I just hope such an offer is being extended to every player at the table. Why shouldn't the fighter be given a chance to present a plot hook? The wizard? Cleric? They all should be given equal opportunities to contribute to the story.

Thanks. I know, right? And I will definitely be playing as one of the assassins in your game. Just sayin'... ;)

You seem to be implying that the warlock fluff indicates the class comes with consequences. Out-of-character personality conflicts, differences of opinion, and playstyle expectations should never be dealt with in-game. At least IMO.

What consequences are the other PCs being asked to potentially deal with in exchange for their class features?

Since you are inserting "feat-like features" as proxy, why not replace the assassin infiltration feature with the benefits of the skulker feat? That feat practically screams assassin, anyway.

I went with Guidance, Resistance and Thaumaturgy.

We generally run overland travel as vignettes showcasing interesting instances along the way. There are lots of scene cuts and handwaved time. What happens in those off-screen downtimes can help explain resource loses or expenditures. They just aren't worthy of playing out.

I've been thinking about how some people like the alternate method of Short Rest = 8 hours, Long Rest = 1 week. I admit it doesn't work for my table's preferred playstyle. And that's okay. But then I'm also considering changing how I want to handle overland travel. In a campaign where the PCs...

I'm at a loss as to how to respond. You seem to be speaking as if from some position of authority on what is or isn't a valid opinion. I don't recognize said authority. Nor do I believe you even really understand my post and my opinion. So, all I can do is say, thanks for taking the time to post...

This is an all-too-common white-room tactic. Pick one. Which ideal version of the fighter are you going to prop up in the moment this time to win this "competition"? A minute ago he had the duelist style. And the war cleric can fight with two weapons as well. Again, I want this bit pointed out...

Given that this is a trinket you've presumably had for some time, I think the point of the unopened letter is to concoct an interesting RP reason why you've chosen to keep it but not open it. Not that you'd want to open it the moment the curtain rises on the very first scene of the campaign. But...

All this shows is that your fighter appears to have wasted class feature resources because they both need the same number of hits to kill a goblin or kobold. Efficiency is also a trait of experts... I really want to highlight this particular response. I hope everyone reading this debate takes a...

Very this. All of it. I am still greatly enjoying playing my half-elf acolyte assassin/shadow monk/feypact bladelock. He's a member of an elite secret sect of the elven fey-church in our world. The Unseen are holy assassins of a sort (thus rogue/assassin), their bodies honed into living weapons...