New Mustachian seeking advice on debt repayment v. retirement v. savings

[stackofshort]

So, after a lifetime of abysmal financial decisions, things are starting to look up. I'm new to the Mustachian lifestyle and the idea of early retirement and am officially smitten. I've had several big life events and changes come my way but am starting a new gig as an independent contractor next month with a $20,000 pay raise and need a little Mustachian advice on how to proceed to get on track.

Here are my basic stats:

Age: 30
Marital status: Single
Salary: $70,000
Debt: $53,000 ($40,000 student loans / $13,000 high-interest credit card/medical)
401k balance: $3,000 (just started contributing in January 2016)
Monthly living expenses: roughly $2250 / $27,000 per year

In late June, I am set to receive a $6,000 check from a settlement and have designated that to go towards credit card and medical debt. This will leave two credit cards with the $7,000 remaining balance (I know, I knooow) and my $40,000 in student loans. I am looking to pay these all off within 2 years or less.

I've made spreadsheets on top of spreadsheets to figure out how to pay off all my debt by July 2018. I still have about $500 or so left over each month to work with within this plan. Should I be less aggressive in my student loan repayment and divert some to go towards maxing out retirement and health savings accounts? Or should I just put the remaining $500 into a savings account? Or should that $500 go right back into faster debt repayment? I'd hate to miss out on two years of potential interest and investment, but debt-free is also the most delicious idea in the world. I also know I am way too new to this area and am open to guidance/suggestions.

TL/DR: Newly working as an independent contractor at $70k a year. After rolling over a tiny newbie 401k to Vanguard next month (Investor shares in VTSMX?) should any extra money go into more aggressive debt repayment (currently budgeted to pay off $47,000 by July 2018) or go towards retirement (what accounts should I be opening? Traditional/Roth IRA?) or should it go into savings (again, account recommendations)?

Please and thank you!

[MDM]

Stackofshort, welcome to the forum.

Keeping it simple for now:
1. Invest up to the maximum employer match in your 401k (assuming the match percentage is higher than your CC interest).
2. Pay the minimum on all loans except for the one with the highest interest rate.  Put all extra cash to paying that off.

See http://www.vertex42.com/Calculators/debt-reduction-calculator.html - you can download a spreadsheet and compare with yours - for the interest cost of different repayment strategies.

[stackofshort]

Thank you! I should add that because I'm now an independent contractor, I will lose my employer-sponsored 401k plan. I did the max contribution/match starting in January but this month will be the end of that brief ride. Any suggestions on retirement accounts I should open in lieu of the 401k are welcomed! 

[MDM]

Thank you! I should add that because I'm now an independent contractor, I will lose my employer-sponsored 401k plan. I did the max contribution/match starting in January but this month will be the end of that brief ride. Any suggestions on retirement accounts I should open in lieu of the 401k are welcomed!

If your CC debt has ~20% interest, then paying that off is better than retirement accounts.

See the 'Investment Order' tab in the case study spreadsheet for more details.

Good luck!

[Jeremy E.]

As a new mustachian if you don't have Employer match towards 401k, I'd just go into full debt repayment mode until you pay off all debt with more than 3% interest rate, starting with the highest interest rate debt first. Once this is done, you can check back for more options, you'd likely want to open up an IRA at that point, but some sort of 401k or 401k alternative might be available as well.