Depends on the bleed every month. A human doesn't need to bleed out every drop of blood to die. At some point, the life support system will simply fail due to lack of it. Same with the server.

When you speak of short term health vs long term health. You have to consider you won't have a long term at the rate it's going.

Once a server is dead...it's dead. Resuscitating it is going to be very very hard. Gambling on how much population the server can sustain before everyone gives up is risky business.