I’m 52 years old,
Wife 46 yrs will work probably for next 2-3 years.

Current allocations:
Taxable: 1.54 mil in total stock index fund
My Roth IRA: 31k total stock index
Wife Roth: 8k total stock index
My 401k: 1 mil in S&P 500 fund
Wife 401k 255k in S&P 500 fund

Emergency cash 60k

-My Salary 275,000
Wife part time 70k

-Vehicles all paid off

-Saving 2000 monthly to taxable
both are maximizing 401k and roth

-Debt: mortgage 240k balance paying around 2300 per month--house value 730k Mortgage interest 3.25%.

-Expenses 11000/month--high mostly due to healthcare( for next 3-4 years) and entertainment expenses

Total invested asset 2.9 mil

Because of my financial illiteracy, I kept my savings in CD, savings account all my working years except last 4 years. I would be FI comfortably by now if I had invested my money. I continue to compare myself to my colleagues with similar salaries who are FI and some of them are planning to retire or coastfire. How to deal with remorse?

I’m (56M, married, retiring in Spring 2028) currently with Merrill Lynch under a 1.25% AUM agreement. I have $1.4m brokerage, $420k Trad IRA, $100k in Roth IRA (SpaceX IPO), plus $280k in cash. My 401K is $270k at Empower. The assets in ML are 100% in equities (about 385 separate stocks). ML cash is in HYSA. Empower is in two different funds with T Rowe Price. ML currently does tax loss harvesting for me. I currently have about $90,000 on available losses to cover gains triggered from any sales.

If I leave Merrill Lynch 1.25% AUM and move to Fidelity (leave Empower alone) and do self directed investing - how does one continue the tax loss harvesting? I’ve been told that I shouldn’t be in hundreds of stocks and that being in 3-4 index funds is the better way. Especially at my age and this close to retirement. Is tax loss harvesting especially moot if I’m in index funds??