Can we look forward to being dead, self annihilation? Seems like we should be able to, but I'm not sure that we can without confusing ourselves about selfhood. Does anyone say we can't?
I don’t find myself in a position to say what happens at death. I have had a near death experience where I was pretty much dead then brought back. For me it was not like going to sleep. It passed by instantly. One moment I was being rushed through an ER to an operating room, it faded out quickly, then immediately faded in just like a movie and I was somewhere else. It was like time travel. I suspect the next time will be similar. It will fade out then immediately come back somewhere else in time where there is a brain similar to mine in the past or future, which could be anyone, or perhaps some other life form. Or perhaps this same body in the past. It is possible that we live the same life over and over playing out different possibilities. I don’t know. If that is the case and there are no souls or higher powers controlling where our consciousness ends up, then death might be something better or something much worse. You might wake up as a pig in some horrible factory farm or lab animal some psychopathic scientist is torturing. It may be the case that all things that are conscious are really the same consciousness living through each life one at a time. These lives are all permanent fixtures of spacetime. I don’t see any reason why our consciousness couldn’t move around in time or take different forms. It is usually the case though that whatever life we are in can be improved. We are in a state of ignorance about what is going on. There could be some sort of reason or test we have to go through. I’m not sure why so many people appear to be so certain that they know what is going on or what is going to happen.
It is possible. Read the experience of Ramana Maharshi.
Generally, the phrase "look forward to" is used to mean to anticipate a pleasant or at least desired experience. So, whether or not one can look forward to being dead will depend on what being dead means.
If being dead is meant in the materialistic/naturalist sense, then no, one cannot look forward to a period in which one will have no such experiences--nor experiences of any kind.
If being dead is meant in some kind of supernatural account in which the person (in the form of a disembodied consciousness or something like that), though not biologically alive as before, does have experiences, and those experiences are pleasant or desired, then yes, one can look forward to those experiences.