Hi,
This is my first time posting on one of these boards and I thought I would throw my two cents in.
As a background, I also live in DC and I turned 29 in May and started out 42k in debt at 22 after college. I now have a net worth between 300-400k via hard work and smart investing. Take my recommendations as you will.
First off, DC is a good city and honestly, congratulations for managing a low rent/grocery/cost of living. That being said, there are some tweaks you could do.
If there is anything you could do to reduce the medical expenses of 500 a month, that is a strong recommendation. See if your employer maybe has a tax advantaged health saving account that could cover that expense. Using pretax dollars or getting the expense as partially tax deductible would save over $1000 a year, if possible. Same with switching providers or if it is a past medical bill, see if the owner of the medical debt would settle for a cash payment now at a great discount. IE, if you owe 10k in medical bills at 500 a month, see if they would accept 7k or less now. Just a thought.
If you want to streamline your monthly bills:
Metro PCS and Virgin mobile have plans for under $40 a month and will often give you a free lower quality smart phone. If having a high end phone isn't a priority for you, you could sell your current phone and save $30 a month.
A small handful of DC places have women's haircuts for under $25 (my girlfriend didn't believe this until I showed her).
As for internet, I always recommend no contract internet. FIOS and RCN (if available) have good deals occasionally. I pay 60 a month with no contract through FIOS for 300MB connection. If RCN is available to you, they have a TV and 150mb special for 30 a month.
Your utility usage looks good, but you could always shave off a bit on electricity here and there. All in all, that could save you more than $50 a month.
Now onto the heart of the matter. You are a saver, but I think you should become an investor. If you want to FIRE at 40, your retirement accounts don't really matter. They act as a great boost and safety net at age 60 and can be used to help on a down-payment on a home in the near future (which I recommend, if your projections place you at over a million when you are able to withdraw). At 40 or 30, it doesn't help too much with living expenses.
If my math is correct, you have you have a net worth of just over 60k. You have 44k in taxable accounts/now money and 26k of that averages <1% a year. Even with 10% returns on your mutual funds, you will average around 4.5% pretax gains per year (around 2000$). Take out your 25% tax rate plus DC taxes on capital gains, that is realistically under 3.5% actually gained with inflation being over 2%. So your money is effectively growing at 1% a year.
This next piece of advice will have some potentially strong disagreement. First thing, find your credit score. Use Credit Karma or check the free annual credit reports or potentially your credit card/USAA reporting. If it is above 720 (or 750), then you are definitely doing fine for the building of credit. You have years of student loans and years of credit cards to build it. The auto loan won't raise your score too much if you are already in the 700's. I am assuming you have a 2008 civic or accord or something with a resale value under 10k (most likely under 8k as all DC Craigslist 2008 'Honda's' are 7k and less). That is $1100 a year in insurance in case your 10k car gets totaled in an accident that is your fault. If you have a 1k deductible, then you would spend $2200 in a year to receive $7000 if you cause an accident, otherwise you spend 1100 a year for risk tolerance.
Since you are receiving 1% on your investments, I think paying off the 9k would be a greater return on your money and once the car lien clears, drop to liability insurance. My 6 month liability insurance is around $200 through USAA in DC. You are currently paying 350 a year in interest payments and you are paying 550 a year via comprehensive insurance while your 9k in savings is earning 90 in interest a year (maybe 65 after taxes). If you pay off the loan and drop to reasonable liability policy (with say $300 for a six month policy, split by 2 people), then your 9k will effectively "yield" more than 5% (or return 500 back a year "tax free" vice $65 after taxes). You have enough money saved up to buy a comparable used car in case of totality.
And for investments, I can't stress enough to learn about as much as you can, especially if you find or like niches. If you are completely risk adverse, Navy Federal (I assume you can get membership since you are USAA) has a 3% CD for I think up to $3000. Numerous other savings account pay over 1% and offer a $100+ cash bonus if you deposit x thousand with them and hold it for 3-4 months. You could open savings account after savings account, maintaining the average 1% rate while collecting a few hundred in bonuses (and with that, actually beating inflation). If you want to step up the game, you could get into credit card churning (though this will initially hurt your credit score, it might improve it in the long run). CC's offer bonuses if you spend x money in y months. Charge everything, pay it off at the end of the month, and reap the benefits.
For higher level investments, I recommend Motif since you can buy other people's basket of stocks based upon whatever criteria you want. Split half motifs, half mutual funds with a comfortable amount in your savings accounts. Maybe you could increase your annual real gains from 1% to more than 5% (maybe more than 10%). You could also invest in some dividend stocks if you like "interest". O Realty is a monthly payment and WRE is a DC reit (It is actually possible to live in a building owned by WRE that you are a partial owner in...so your rent goes into your future dividends in a sense).
If you like Niche markets (for >10% gains), I recommend looking into Fundrise, Upfund, doing mock trials for DC law firms, going to estate sales and scouring the craigslist free section. Within the past few months via CL, I have picked up 2 free mirrors within walking distance, cleaned them off with a paper tower and windex and sold them on CL for 50$ and 75$ within 3 days. Last week, I picked up a set of actual copper pots and pans for free that just needed to be scrubbed with salt and vinegar. At an estate sale, I bought an entire drawer of miscellaneous silverware for 3$. Some of the pieces were actual silver (estimated melt value at the time was about 90$). The Ebay resale value piece by piece was around $450. All of that for a 3$ purchase.
Those are my current recommendations on things you can improve upon. I have had success with my own philosophies. Feel free to reply or message me if you want me to keep talking as I do live in the same area.