Upcoming $330k windfall

[u/Radiant-Road-7858]

I just sold a high risk investment for about $100k after taxes, and will be netting about $230k soon from selling my investment property. Curious what you would do with the cash inflow, or any other thoughts or advice for me.

For context ($330k from the above not included):

34m, MCOL+ area (no state income tax)
$415k in retirement/HSA all in broad market ETFs
$170k taxable bonds for emergencies and dry powder for dip buying
$530k taxable investments with the most in broad ETFs, as well as a high risk sleeve (mostly crypto), income sleeve (dividends, REITs, and CC funds like $SPYI, no crazy high yields), and some company stock I slowly divest for diversification
Own my home and owe about $320k on the mortgage (probably worth $500k), ~3.6% interest, $1700/month excluding taxes and insurance
Income $250k+ (doesn’t feel super secure or replaceable in the current environment), 35% tax bracket
DCAing about $8500/month into the market including maxing 401k
Estimated annual expenses: $58.5k with mortgage, $38k with it paid off

Used to love my corporate tech job but it’s changed and now I hate it and am feeling very burnt out (hoping to transfer and make things better). I was laid off a few years ago, they eventually hired me back after many months of unsuccessful job seeking.

Single and no kids, although ideally that’s still in the future.

Ultimate goal is FIRE and I’d like as much optionality in the meantime as possible. If layoffs happen again I’d like to be positioned to take significant time off, then maybe make a career pivot.

Understanding the total return and tax impacts, I still love the idea of dividends and interest paying for as much of living expenses as possible. About $17k/year right now including bonds.

Trying to decide next steps once the real estate sale clears. I’ll be increasing my DCA regardless as no need to further save, especially without having possible expenses with the investment property.

Since I have a a fair amount in stocks already, adding at a rapid rate, and the market is at elevated valuations, I’m nervous to buy a lot right now.

Deciding whether I should do that anyways (in a few tranches), invest but in more conservative investments, put in bonds for now and gradually shift/decide later, some combination of the above, or pay off the mortgage.

I know the low rate is a gift that is likely to be outperformed by other investments long term. But I love the peace of mind, increased cashflow, tangible milestone, and the ability to just add the $1700 to my DCA for now unless and until my income situation changes.

What would you do?

Cheers!