u/Dry-Wasabi-1450

Currently in my early 30’s married with 2 kids with HI of roughly 500k in HCOL.

Although my job and my wife’s job are mostly stable (whatever that means nowadays) I have felt generally burned out lately and considering a career change. Given this, I have been holding 250-300k cash since 2024 as a rainy day fund to give me runway for e.g changing careers or opening a business.

Given the recent bull run, I cannot stop feeling remorse about the missed gains (50%+) but yet again don’t know what I should do now.

If you were on my shoes, would you just dump it all on the market, knowing you may want to use the money to do something eventually or just accept this as the cost of uncertainty?

I am already maxing all my tax advantaged accounts and investing extra new cash monthly

I have been dreading car shopping for a while but finally pulling the trigger after being stuck in the freeway again.

Calculators & tools online mostly help guide around the maximum purchase price but I found them pretty useless for HE.

Current HI is around 500K but feels unstable nowadays (tech). I’d probably buy cash to avoid stressing about monthly payments.

1. How do you weigh car purchase price against other goals? E.g saving for a downpayment

2. Does it ever make sense to just buy new, even though it is on paper a worse deal just for the peace of mind? I figure with the difference in price I could afford any repair, but I truly hate dealing with car repairs, negotiating, researching, etc.

3. What kind of car price range would you consider if you were in my shoes? What is a reasonable purchase considering a 2 car household? Average cars are so expensive since the last time I looked in 2016-17!