Here is my dilemma: One of my articles ranks very well on Google's first search page when someone searches for a certain keyword. Unfortunately that content is not relevant anymore nor most accurate. Can I do a 301 on that article to one that it's relevant? Will I see a drop from that high position? Thank you
Yes you can do a 301 redirect. its the best way. Your rank may drop in the first weeks but after google uodate servers it will go back to normal.
Using L301 Redirection will pass the value to the new URL. However, your ranking might suffer a little bit so it's more advisable to redirect using L302 first till the new URL get's indexed in various DC's (If it's not yet indexed) and then switch to L301 redirection. A good tactic is to update every backlinks pointing to the old URL so it points to the new one though Hope i was helpful, REP is most appreciated.