Pay yourself first, if possible have it taken directly from your pay before you see it. No matter how much or how little you earn, if you have a budget and keep to it, you will meet all your goals. Don't feel you have have have large chunks of money to get started, everyone started somewhere.
1) Pay down any revolving debt you have (credit cards, etc). You can't have these obligations hanging over your head as when you are paying the 10-18% interest on the balances, that is money you are not able to save.
2) Retirement savings should be your number 1 goal. 529's etc will have to come 2nd.
3) Vanguard is a great choice. You may contact them for advice in setting up a portfolio and pushing money into it each year. Roth IRA's are great as the money will come out, tax free, when you start using it in retirement.
4) Take advantage of any work retirement plans (401k's etc) and get the maximum match they provide. That is "free money" just for participating. When/if you get raises, increase your contribution as you will not miss it.
5) Using flex spending accounts for your medical (sounds like you are) as the tax savings are great.
6) There are many tools to input what you have done to see if you have the right balance. Most people your age should have a 75-25 to 80-20 stock/bond mix. You can go with more aggressive holdings in this mix if that is your style. You do have time on your side, so I would suggest being aggressive with how you pick stock funds.
7) Mutual funds are a great way to start. If you get some equity built up, you may start looking for individual stocks to buy. I like dividend paying blue chip stocks which have been around. I don't look for the next big sector or hit when it comes to individual stocks.
8) Keep talking to others, keep reading, go to free seminars and maybe even meet with some financial advisers...you may pick up some useful tools along the way. Your workplace may offer face to face meetings with the group that sponsors your retirement plan, another good option.
You can accomplish a lot on your own and if it does become more complex, then you can seek advice and help then.