Advantages (GDT Round 1)

Senji VS Terryman:
+ Equal or better endurance and durability.
+ Piercing demolishes his resistance to such things. Can cut through steel.
+ Crow Claw is extremely accurate and can take out vitals.
+ Grapples should be no problem.
+ Can pierce from afar.
-Far weaker striking and grappling (mostly inconsequential)
-Terry can fly. (Eh.)
-...I think that's it.

Senji VS Gourry
+ Piercing attacks overkill Gourry's piercing resistance.
++ Piercing from afar turns this into a decent advantage.
+ Definitely durable and persistent enough to withstand most attacks and keep fighting.
+ Antimagic does absolutely nothing here.
- Slashes from the Sword of Light will be a potential problem up close.
-Beams from the Sword of Light will give him trouble at a major distance.

Senji VS Neptuneman
+ Equal or better endurance and durability.
+ Piercing demolishes his resistance to such things. Can cut through steel.
+ Crow Claw is extremely accurate and can take out vitals.
+ Grapples should be no problem.
+ Can pierce from afar.
+ Possesses nothing that can be magnetized immediately.
- Far weaker striking and grappling (mostly inconsequential)
- Neptuneman can fly. (Eh...)
- Magnetism will become a problem if the fight is prolonged.
x Both of them can take a ridiculous beating.

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Jackie VS Gourry
+ Clearly much faster.
++ Be sure to specify that his -movement- is low enough for the tier, but that his combat speed and reactions are superhuman.
+ Should have no problem damaging him with piercing.
++ Should also have little problem withstanding his piercing attacks.
+ Hilariously more versatile.
+ Summoning multiple Darklings can most likely overwhelm him.
- Weaker physicals in general. (by design, won't matter)
- Sword of Light WILL one-shot Jackie despite his piercing durability. (shouldn't matter)
- Beam attacks from the Sword of Light would keep him on his toes.

Jackie VS Terryman
+ Clearly much faster.
++ Be sure to specify that his -movement- is low enough for the tier (meaning he's not impossible to tag or capable of blitzing with impunity), but that his combat speed and reactions are superhuman.
+ Should have no problem damaging him with piercing.
+ Hilariously more versatile.
+ Summoning multiple Darklings and tendrils can most likely overwhelm him.
+ Massive advantage at a distance.
- Weaker physicals in general. (by design, won't matter)
- Terry can fly. (Eh...)
- ...I think that's it.

Jackie VS Neptuneman
+ Clearly much faster.
++ Be sure to specify that his -movement- is low enough for the tier (meaning he's not impossible to tag or capable of blitzing with impunity), but that his combat speed and reactions are superhuman.
+ Should have no problem damaging him with piercing.
+ Hilariously more versatile.
+ Summoning multiple Darklings and tendrils can most likely overwhelm him.
+ Possesses nothing that can be magnetized immediately.
- Weaker physicals in general. (by design, won't matter)
- Neptuneman can fly. (Eh...)
- Magnetism will become a problem if the fight is prolonged.
- That endurance is going to be a major issue.

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Death VS Neptuneman
+ Equal or better striking.
+ Piercing with Harvester beats Neptuneman's piercing resist, especially in Reaper Form.
+ More versatile.
+ Ranged weapon falls under the same description as the one that punches through Chojin piercing resistance.
+ Healing factor is a major advantage due to Neptuneman having no piercing/slashing attacks.
- Weaker grappling (mostly inconsequential)
- Magnetism may be a problem.
x Both can take a ridiculous beating.

Death VS Terryman
+ Much more agile and capable of dodging things.
+ Harvester's piercing/slashing (especially in Reaper Form) >>> Terryman's resistance.
+ Ranged weapon falls under the same description as the one that punches through Chojin piercing resistance.
+ Healing factor is a major advantage due to Terryman having no innate piercing/slashing attacks.
+ Despair grants a decent mobility advantage.
+ Ghouls will overwhelm if summoned en masse.
- Weaker grappling (mostly inconsequential)
- Terry can fly. (Eh.)
-...I think that's it.

Death VS Gourry
+ Harvester is more versatile at close range than the Sword of Light.
++ Harvester and the Sword of Light have comparable piercing/slashing feats.
+ Healing factor.
+ Generally more versatile.
+ More agile and acrobatic.
+ Despair grants a decent mobility advantage.
+ Ghouls will overwhelm if summoned en masse.
- Beams from the Sword of Light are likely to be more reliable than Redemption at a distance.
- May have to mount a counterargument if opponent claims that "Holiness" will kill Death for some reason.

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3v3 Advantages

Senji
+ His Branch of Sin is more than capable of getting through the opponent's piercing resistances.
+ Extreme durability and endurance will make him hard to deal with quickly.
+ Will dominate at mid-range due to the sheer piercing of his Crow Claw and his ability to use it across a short distance.
+ With Jackie as a priority target, he becomes much more dangerous.
- Lacks good range. (Only really matters against Gourry, but whatever)
- Lacks good lifting and striking feats to contend with anyone on the other team. (Shouldn't matter)
- The least versatile person on the team. (The others make up for that.)


Jackie
+ Can potentially keep most of the team busy with Darklings and tendril spam while the others clean house.
+ Has enough versatility, speed and piercing to survive any early-fight 1-on-1 encounter.
+ Most acrobatic combatant in the entire fight alongside Death.
+ Portals will allow him and his team greater battlefield control.
+ His tendrils mixed with Senji's Crow Claw are going to be a lethal combination.
- Extremely susceptible to being one-shot if he's caught in the wrong place.
- Won't be able to do much actual damage on his own.

Death
+ Extremely well-rounded.
+ Both Harvester and Redemption should be good enough piercing options to kill anyone on the opposing team.
+ The second most versatile character in the entire matchup.
+ Healing factor is a major advantage due to 2/3 opponents not having innate piercing/slashing attacks of their own.
+ Despair grants a mobility advantage.
+ Most acrobatic combatant in the entire fight alongside Jackie.
+ With Jackie covering from a distance and Senji dealing major damage at mid-range, he can freely choose between long-range and melee engagement, supporting either as necessary.
- Only has one real ranged option.
- Lacks relevant grappling feats for melee encounters. (Mostly inconsequential.)
- May have to mount a counterargument if opponent claims that "Holiness" will kill Death for some reason.

The Plan

1. Immediately upon engagement, Jackie begins summoning Darklings and tendrils to assail the other team. As these Darklings and tendrils will number in the dozens to hundreds, they won't be easy for any of the characters to simply run through no matter how large the difference in stats is.
2. Being forced to deal with the Darklings and tendril spam will give Senji and Death time to get their offenses started before the other team has any bearing on the situation. Senji will eviscerate with his Crow Claw at close to mid-range while Death switches between assaulting individual targets and supporting his teammates in engagements at their respective ranges.
3. In the event that any of the characters deal with the overall ranged advantage long enough for melee to become an issue, each teammate is capable of covering for another's weaknesses and driving off threats to their person together.
3.5. In the event that the team finds itself overwhelmed, Jackie's portals will allow for a strategic exit, which will give the team a chance to come up with a second attack strategy that accounts for the other team's capabilities and weaknesses.