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Flukenest and Shaman Stone can do a lot of damage.
Also;
Upgrade your Nail to the Channeled Nail,
Upgrade your Vengeful Spirit to Shade Soul,
Upgrade your Desolate Dive to Descending Dark,
EDIT: Wait you have the achievement for defeating Soul Master, so how do you not have Desolate Dive?
already got it:P i thought the explosion
Desolate Dive is upgraded into Descending Dark at the Crystalized Mound, which is in the bottom-right of Crystal Peak.
Vengeful Spirit is upgraded into Shade Soul at the Soul Sanctum. You need to get the Shopkeeper Key from Crystal Peak (in the room just left of the Crystal Guardian bossfight), then bring the key to Sly. Then buy the Elegant Key from Sly and bring it to the Soul Sanctum. Use the Elegant Key to open the glistening metal door, then initiate the Soul Warrior bossfight. Defeat the Soul Warrior and proceed passed the boss arena to find the Snail Shaman that has the spell.
Howling Wraiths is in the Overgrown Mound, which is in the top-left of Fog Canyon.
Howling Wraiths is upgraded into Abyssal Shriek at the altar in the bottom-left of the Abyss.
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Shade Soul is pretty good for the Grimm fight. Especially when you equip Shaman Stone and Flukenest.
Abyssal Shriek can be good for hitting him in the air above you, though more so in the Nightmare King fight.
The warrior dreams get a health up at every nail level, while Grimm only gets them for the last 2.
The earliest example of this is the Husk Sentries in the City, whose health increases slightly when you get the Sharpened Nail, because otherwise you'd kill them in like 2 or 3 hits.
That said, you can still take on the boss at any stage in the game. These additional upgrades just make the boss a little easier for you.
With everything said and done, it looks like the devs increased the boss health to prevent the fights from becoming too trivial, but not so much that it overwrites any benefit you have from getting your weapon upgraded. In other words, you still make boss fights easier by choosing to upgrade the nail, but it's just not as easy as using a fully upgraded nail vs an non-upgraded boss. It's a good move I think.
All you have to do is dodge
hit him right after he does the spike attack
pogo him if he tries to dash you and hit him again if you get the chance.
if he does the uppercut you have the option to either dash away or try to hit him, I usually play it safe with this particular attack.
for the bats, jump over the first one, walk up to him and smack em'.
Then there's his bullet hell attack, you'll need piccolo's advice for this.
Mark of pride just makes hitting him safely easier, you could even slap longnail on there if you wanted to.
I found quickslash to not be very useful on both grimm fights, since you can only really hit grimm so many times before he attacks again.
Look at his patterns, he's very consistent in what he does so once you learn all of his attacks you won't be caught off guard. You don't get many windows to actually hit him, but the post above describes when you do pretty well.
Mark of pride is good if you feel more comfortable with increased range, Quick Focus would probably help if you think you take too much damage and need to heal a bit more. One thing I've seen people do is have the Nailmaster's glory charm and charge up Great slashes to deal much more damage to him.
I treat it as the moment he spawns in the middle to do it I dash towards the closest wall and wait there. You typically don't want to be hugging the wall since sometimes dodging requires you to move back a bit to get enough time in. A lot of those are either long or short jumps, some of them double jumps, and sometimes even standing still as I've had plenty of runs where half of those just went over my head. You could also dash through them, but I prefer jumping.