When should I fight "Lost Kin"

[Hoppled]

I beat his younger brother's ass attempting for a whole hour. I was like dam.. that was hard enough. Then I go into the dream world and this dude is like him but harder... I cannot see how I'm expected to beat something this difficult.

I have 1 nail upgrade so far and not that many masks. I enjoy challenging fights, but this will take me hours.

[(Edgy) Asriel Dreemurr]

I would at least get the Coiled Nail and Defender's Crest Charm.

[f001er]

He is not that bad once you get used to him, but yeah, you probably want at least 1-2 more nail uplgrades if he seems too hard for you. Then you can just damage nuke him.

[Fenfen]

Once you get the upgraded dash he becomes a lot easier. If you want to do it before then I suggest the defender's crest, thorns of agony, long nail/mantis pride and if you still have free notches then just toss in whatever.

[Scraps]

Lost Kin is the middle-ground dream fight, in my opinion, and I strongly discourage charms that "reward" you for tanking hits, like Thorns of Agony, Baldur Shell, Grubsong, etc. as Godhome content leaves little room for error the further you do that DLC.

My recommended charms for first timers are Mark of Pride for range, Quick Slash to quickly dispatch infested balloons, and Sharp Shadow to counter Kin's dashes. Lastly, but most importantly, equip Fragile Strength (replace one of the 3 notch charms if you don't have enough), as the Fragile Charms will not break in dream instances.

I can't give too much advice regarding nail upgrades, since I'm very comfortable fighting Lost Kin with 1 upgrade.

[JapanGamer29]

The Defender's Crest charm kills all the floating fire ghost things for you so you only have to worry about Lost Kin. I also recommend Mark of Pride for reach, and Sharp Shadow is amazing for this fight. You never even have to jump, just dash through him when he dashes at you (watch for his wind up).

[Krispy]

fighting him early is the best way to prepare for the more difficult bosses later, practicing hitting his ad spawns as well as him while dodging is VERY helpful for late game, so I would keep trying him at the point you are at and if it becomes to tedious then move on and come back later