Excellent start. I have a good chunk of military finance experience (LCDR type). The most important piece of advice is STAY AWAY FROM FIRST COMMAND FINANCIAL and other financial advisors who do more harm to young military. Also, don’t buy a time share, whole life insurance, universal life insurance, or basically any life insurance product except your SGLI. and for the SGLI, you could probably lower it to $50k from the $500k to save $40/mo, but that is up to you.
For starters, I don’t think your stipend qualifies as earned income to qualify for a Roth. Your summer training does though. So if that meets the limit, great. Otherwise, you are limited to contribute to the Roth what you earned via a W2 (rough rule of thumb). So be careful with that.
Excellent use with the MLA/SCRA. I highly recommend that if you are financially trustworthy and will not go crazy spending since you have a credit card. Also consider the Chase Sapphire Reserve; fee also waived.
Look into the cadet/midshipmen loans. 10-15 years ago, they were like $20k-$40k between 0.99%-2.99% interest. I don’t know what they are now, but if that is similar, consider taking it out and putting it in various 5% treasuries and CDs. This might also be a reasonable emergency fund or enough to give you breathing room to start investing your income or in real estate.
Look into househacking. When you are young and single, you likely can deal with the annoyances of having a roommate or shared wall. Look into buying a quadplex or duplex at every duty station >2 years you go to. Use your VA loan and create a small real estate empire. I wish I started that at your phase.
As for selling stocks and going to Roth, both of those amounts don’t have much taxable impact now and you will need some money to spend for the next 30-40 years. Either way, won’t make a drastic dent in your future. That being said, when you Commission, do everything you can to max out your Roth TSP to the ~$23k limit and Roth IRA to the $6k limit. If you can sacrifice that much as an O-1, that will do incredible things for your future growth. That is likely more impactful than waiting until you are O4 over 10 and investing the excess.
