So how does the dlc fit in the continuity?

[Planguy]

Alternate universe? I figure Loremaster might be Azazel but is it an alternate universe where she took over hell or is it later in the standard ending? Doesn't really make sense when they're in the human world. Maybe Helltaker lived a normal life, died of old age and then the harem members went back to hell and Azazel did her takeover plan? Whatever the case may be she went full demon, even if she isn't aware of it or is in denial.

[Slashley]

In Helltaker lore, very, very, veeeery old Demons eventually have their horns turn white.

Have a look at Justice in the base game, and Justice in the extra content.

[Keoul]

Future.
It follows along the comics vanripper has been uploading on twitter.

[ekisacik]

Most likely it follows the Abysstaker ending, but it's in the far future, long after the protag is gone. Judging by the ingame line from that ending, "Death is no longer a concept, either", it's safe to assume the protag is with Beel in the abyss while hell has been taken over by Loremaster.

[Sunday Driver]

What if examtaker and helltaker is the same person?

[Dr Birb]

Originally posted by Hoxilicious:

What if examtaker and helltaker is the same person?

no

[Dr Birb]

Originally posted by ekisacik:

Most likely it follows the Abysstaker ending, but it's in the far future, long after the protag is gone. Judging by the ingame line from that ending, "Death is no longer a concept, either", it's safe to assume the protag is with Beel in the abyss while hell has been taken over by Loremaster.

That ending quote has no connection at all. It doesn't say anything what timeline it could be. As for now, I see no evidence to disprove either.

[Svintoo]

It is in the future in the same universe. Not sure if it follows the normal or abysstaker ending though.
This is explained in the artbook unlocked when clearing Examtaker.

[Depressed by Joji]

void ending is canon

[Planguy]

Aw, there isn't going to be any kind of dating sim type game in the setting? It's going to be a bad future type thing? Or could there be other games in the "Pretty freeloaders" ending?

[Dr Birb]

Originally posted by Planguy:

Aw, there isn't going to be any kind of dating sim type game in the setting? It's going to be a bad future type thing? Or could there be other games in the "Pretty freeloaders" ending?

He can do anything, go forward with Examtaker plot, go back with it or go back to regular timeline since both are equally canon.

[Gena Cider]

examtaker is the aftermath of all the latest comics, and they all take place on the abysstaker timeline where helltaker entered the portal and is now gone.