re: Am I okay with my current financial situation to join a country club?

Don't over-complicate it.

If you can meet your short- and long-term goals while also paying to go to your country club, then do it if you want. Like someone else said, if you join and feel like it's too much, resign your membership. Problem solved.

Consider also how much quicker you might be able to reach certain goals if you use the $280 elsewhere. That may be a reason not to join.