It is a "game" you play. When I ask for a specific room I shoot for a good but not best room. Simply because good is relatively easy to get assigned ahead of time as hotel usually has several of those and they might be able to sell best ones or give for 1 night stays that check-in late.

Basically on several day stays "good" is more likely than "best" and I am ok with "good" when traveling alone and would only go past that when I travel with the family, then I would ask room coordinator or FD manager or GM for a great favor during that stay.

This strategy works good for me.