Due to certain health conditions, I have to undergo surgery which is pretty major with recovery time of ~3-4 weeks. I will also be beginning a new job around the same time. Should I ask my employer if I can move my start date back? However, I will not be able to use insurance if I do this—and the surgery will probably burn through most of my savings. Otherwise, I can take time off right away for a week, and then possibly work remotely for another 2 weeks, but I am worried this will piss off my new team/manager. Or, I can wait a year or so and do this, but my condition will cause me some distress. What should I do?
Don't know about "dump patients in the street," but yes, you need the coverage. Unless it's a startup, any half decent manager will be understanding. Not happy, but understanding. Your work will be affected since it'll clash with onboarding (more difficult remote), but it's the only humane option
February is the best month
Get the op while employed at your old job before you quit!
I experienced similarly before. My case was even worse than yours. I left my previous job and I got hurt on the day before the start date of my new job!!! Exactly one day before that!!! :( My surgery was major and I told my new manager ahead of time. He was pretty nice and told me to focus on recovery first. For insurance, not sure if you heard about Cobra? If no, you should go and check it out. That is a company specifically targets to cover the grace period in between two jobs by extending the insurance from the old company (meaning you can continue using it with the same coverage). I went through Some medical processes on the same day of injury, and those were all covered by Cobra. The actual procedure happened after I joined the new company. And my surgery could be covered by my new insurance in the new company. But due to my old insurance was still in effective, I used the old one for everything together. (If you have already paid full amount of deductible, extension is definitely a better choice). You should definitely tell your new boss about it. And no matter how serious your injury and surgery are, I don’t think a good boss or company would say a direct no to your request because of that. There should always a way to work out this properly. Good luck!
Wait a couple of months + inform your new manager
You can also do it over the holidays to try to maximize time off
Holidays? You mean those that come in December? That's like 2 extra days off