I would think it would be better to have it spread out over a longer time, as surviving farther into the future means you get to see more of what happens in that future

My own musings on the topic have been that the reason one should choose to sleep rather than sacrifice life to stay awake is that you get to see more of the future and be affected by the future. There are many ways in which staying alive could pay off significantly:

• one might make it to the 'actuarial escape velocity', where medicine is extending life faster than you're living it
• one might survive to the point where uploading is workable
• one might live to the point where cryogenics has improved enough that minimal damage is done during the preservation and it will soon be feasible to resurrect one
• one might persist to the point where resurrection is possible
• one might be alive when nootropics and other intelligence enhancements become enough of a win to make up for lost time, or reduce sleep needs with minimal costs (some perfected modafinil?)

Given that losing lots of sleep isn't a neutral thing and damages things beside longevity (mood, intelligence, creativity), and given many likely benefits to surviving, the modest boost in time awake isn't worth it, I think.