“And the God of peace will crush Satan under your feet shortly. The grace of our Lord Jesus Christ be with you. Amen.” (Romans 16:20)
Now this was written about 55 A.D. Was Satan crushed under their feet then, or is “shortly”, like “these last days”, or like “this generation”?
Revelation says Satan is to be bound sometime in the future or is he bound now?
Yes and yes. All three phrases refer to happenings in the first century. It stretches credibility to suggest that "shortly" means some long indeterminate time in the future, at least several thousands years. Just as it stretches credibility to suggest that "this generation" really means "that generation".
Regarding the meaning of phrases like "last days", see Acts 2:17; Heb. 1:2; and 1 John 2:18.
Revelation says Satan is to be bound sometime in the future or is he bound now?
If you allow the Bible to interpret itself, Satan is bound now from deceiving the nations.