Maximizing Tax Benefits: Using Carryover Losses to Offset Gains (T-Bills, RSUs, Shares)

**\[Looking for Advice\]**

I made some mistakes in options trading in 2020, which resulted in a short-term loss of about $130K. I learned from my mistakes, and fortunately, I was able to secure a well-paying job in 2021. Since then, I have saved up about $300K.

I now focus on long-term investments by buying and holding shares (VOO, VTI, SCHD, top tech companies, etc.). However, I have not invested the $300K in stocks because I plan to buy a house within the next couple of years and need that money for a down payment, potential renovations, and settling in. To ensure safe and guaranteed returns, and to avoid state tax on the gains, I have been investing that money in T-Bills. Last year, I earned about $15K in interest (received a 1099-INT) from T-Bills.

While talking to a friend, I learned that if I sell T-Bills before their maturity, the gains will not be classified as interest income (1099-INT) but rather as capital gains, which can be offset against my past losses. For example, if my T-Bill matures on 6/30/2025, but I sell it on 6/25/2025 (before maturity), the gain would be treated as a capital gain rather than interest income.

Since filing my 2021 taxes, I have been deducting $3K per year from my past losses, as allowed by the IRS, and I still have $115K in carryover losses.

Additionally, I have not sold any of the vested shares I received over the past two years, and they have gained approximately 15% (\~$25K).

# My Questions:

1. Would selling T-Bills before maturity be a good strategy to offset my carryover losses?
2. When I sell my vested RSUs (which may have both long-term and short-term gains), or the shares, will I be able to offset the gains with my remaining carryover losses?
3. What other strategies can I explore to make the most of my remaining losses?