re: Where should I start putting extra money every month?

Look at your Vanguard options. See what performed well last year and consider investing equally in the highest 3. Target date retirement accounts have a certain amount of bonds involved. With interest rates as low as they are and The Fed talking about numerous rate hikes, you are setting yourself up for losses on that front. Do you have your emergency fund set up? (6 months of expenses)? Want to learn a bit about some of this? Consider buying Dave Ramsey's book "The Total Money Makeover". Great for novice investors. I agree with the above saying to max out your 401K and be sure you are contributing all of your money to pre tax contributions for maximum tax benefits. Also remember that Vanguard offers you free advice and counseling. There is no shame in saying that you are new to the game or don't know something. Everyone is learning daily.