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Personally I tried it and it’s not that worth it other than getting the empty environment logbook there and the mastery skin.
I have not played in such a way where I got to that level and was not able to beat him so I do not know if dying loses it, but I would trust the other posters and expect that if you do not survive then it won't count and you won't get the skin unlock.
Correct that it does not count because you have not actually obliterated yourself.
The Obelisk instead acts as a Teleporter instead of ending your run, which requires you to complete the boss fight to obliterate. Dying in there acts as dying anywhere else in your run, which results a ♥♥♥♥♥♥♥♥♥-less trip back to the Main Menu.