Dire Fleet Ravager - This one is definitely just a maybe. I like it because of the Menace as this deck does a good job keeping a thin amount of creatures on the other side of the field, and I usually don't do anything to their life total until later in the game so this is likely to drop a fair amount of life which makes the requirement for the size of Hailfire to be much smaller. I think one in the sideboard for Multiplayer or if I'm up against someone that has a bunch of lifegain is all I would actually do since he costs so much mana.
Sword-Point Diplomacy - +4. +4 right now. 3 mana for 3 cards in black with no downside to me? Yup. 3 mana for 2 cards and 3 damage to my opponent? Yup. 3 mana for 1 card and 6 damage to my opponent? Yup. 3 mana for 0 cards and 9 damage to my opponent? Yup. Don't even care that the cards I lose go to exile. This is amazing.
Vraska's Contempt - Solid removal. Gaining 2 life might be sort of relevant, but straight exiling a creature or planeswalker at instant speed is important. I don't know if this is better in the main board or the side board, but I like it. Probably at least 2 in the side? Not sure.
Raiders' Wake - LOVE the effect, disappointed that it costs 4. I really want to have at least one of these, but that cost might not be worth it. It's also too bad that I will likely be creatureless again after rotation so the Raid ability that sort of makes the 4 cost more worth it by adding 2 extra damage and dropping a card right away. I could make a case for Dreamstealer being reliable as attacking for 1 damage, discarding a card for 2 damage and then Raid triggering to discard another card for another 2 damage. Now that 1 damage and 1 card becomes 5 damage and 2 cards. It's not terrible, but it has to happen in that order and pretty much on turns 3 and 4. I want to like this, and I do, but I don't know how reliable it will be.
Kitesail Freebooter - Perfect! Basically a flavor reprint of Brain Maggot except this one has 2 toughness which means Dual Shot can't just kill it! This isn't meant to stay alive forever, it's meant to draw burn/removal and tie up your opponent's mana so that you can just make them discard the card again anyway. These tempo shenanigans really throw off your opponent's plans and strategy and being a two cost to lower the cmc of the deck is sweet. A full set of this will likely replace the much larger and more expensive Thought-Knot Seer and Distended Mindbender. There is so much good discard/removal/draw to support a fully creatureless deck (especially with Sword-Point Diplomacy to refill my hand or add even more damage).
Walk the Plank - Sorcery, but solid card. Two cost and it's dead. Not sure the configuration but I'm sure there will be 2-3 of these somewhere.
Blight Keeper - If I go with more creatures (or have a creatureless mainboard and a creature heavy sideboard) it will play nicely into Raider's Wake, and the 8 cost ability (8...really? 8?) is a mana sink to drain 4 life and possibly save you or end the game. A 1 cost 1/1 flyer is never terrible, especially if it does other things or enables other things. I dunno, just keeping my eye on it.
Duress - Yes! One cost for information and getting rid of a non-creature thing? A reprint I was hoping for. Classic.
Primal Amulet
Flip - I can't believe this is a thing. This is the best reason to play lower cost spells and become creatureless. The discount is nice, but cheap cards like Harsh Scrutiny and Duress don't care. Doomfall for 2 is huge. This will take a turn 6 or 7 Hailfire with X 5 or 6... and DOUBLE it. Cards like this I always include as a 2 of (and by that I mean Pyromancer's Goggles lol). I hope this starts off cheap so I can get a pair, but the fact that it's all colorless and then creates any color of mana means this can be a bomb in pretty much any color deck (most likely Red and Blue).
Field of Ruin - Interesting. I won't need the colorless sources for TKS anymore but this could be nice to deal with Deserts. Kill a desert, we both get a basic. I like it.
So the problem here is that there are a lot a nice new cards, but I'm only losing 13 slots and I want full sets of a lot of these lol. I haven't been using Torment of Venom and Unburden (which saddens me...) so I'll be able to add in a few more. Here's my best guess for what I'll be swapping out:
-1 Blighted Fen, -1 Sea-Gate Wreckage, +2 Field of Ruin (Main)
-2 Distended Mindbender, -2 Thought-Knot Seer, +4 Kitesail Freebooter (Main)
-1 Remorseless Punishment, -1 Ob Nixilis Reignited, +2 Primal Amulet (Main)
-4 Torment of Venom, +4 Sword-Point Diplomacy (Main)
-2 To the Slaughter, +2 Vraska's Contempt (Side)
-3 Grasp of Darkness, -3 Unburden, +4 Duress, +2 Raider's Wake (Main/Side)
Which leaves Dire Fleet Ravager, Walk the Plank, and Blight Keeper on the Maybeboard.
Once I can actually reconfigure the cards on here and test out hands I'll make the final decisions. I think I want to try 100% creatureless for the mainboard with plenty of removal, wipes, discard, and hailfire. The sideboard can bring in the 8 creatures and Raider's Wake and try a different strategy after your opponent takes out all of their removal.
