Hey Ozeus! I don’t think it would be difficult to catch up at this point. Classic is a more simple world in my mind. 1-60 sure is a grind, but if you’re up for the challenge definitely not too late.
If you decide to do it- come check out Vanquish. Alliance side on Heartseeker. We started a few months ago as a re-roll/ leveling guild and we’re over 200 active memebers now. We’re just starting our raiding adventure- so there is plenty of time to get caught up and experience progression with us!