How poor were my choices?

Last year, I left a job making ~55k and partner made ~19k. Had a mortgage (1400), 2 car payments (300 and 350), and the normal bills. We live pretty minimalist. The new job was a massive increase is pay, ~185k. I realize how fortunate I was.

Partner left her job (she was very unhappy) to be a SAHM for our 2 year old. We bought a new house a few months ago to be MUCH closer to my new job (2500 mortgage). I did what I was probably NOT supposed to do and traded in my vehicle. Neither of us have ever had the ability to actually get a vehicle we REALLY wanted. The new payment, a lease, is 1000. Our old house is now on the market.

Now, I think I should do a better job with the money situation. We have plenty of disposable income now. But, I am technically a contractor, so I get ZERO benefits. Medical Insurance is 425 a week and dental is 20 a week. These are through the contracting company, but they pay zero for us. We are not offered any 401k, retirement, HSA, etc. It’s all on me.

My question’s are:

Should I buy out my lease and downgrade the vehicle?

Should I keep the high insurances (open enrollment isn’t until next May) or go with the marketplace? The tax implication is not clear to me.

Looking over the post here and such, I know I should be saving for an ER fund and maxing out IRA’s, HSA (if I can), etc.

Are there any other tips anyone can provide? This has been new territory for both of us and I am worried I am going to creep back up to maxing things out.

Edit: typo in initial salary.

Edit 2: Additional context. I’m a w2 contractor with all taxes taken out. Take home is 2400 weekly. I feel good about job security in my industry. The vehicle is a 75k Tundra. I don’t know the buyout but I did put 8k down. I have regrets there. For medical, no major issues, just a few generic meds. The toddler is the most expensive, we’re already at 3500 Out of pocket with a 6000 max oop. The insurance is killer and hasn’t paid a dime towards any medical visits at all (except 1 visit each for preventative care). We’re actually at 25k total medical (weekly premium and 3 toddler emergency issues) so far with insurance paying nothing.

Just a thank you to all who’ve posted.