Go to a university’s dental school for your care. Half or less of the price, and they do everything. A professor checks the work of the students; they are more exacting than most dentists, IMO. My parents’ dentist and my cousin, also a dentist, recommend dental schools. Dental insurance should not be on your radar right now. To give you perspective, Pitt’s dental school is $42 for a cleaning and exam. Retail is about $100 here.
Try to stock up on your meds if at all possible - buy them now at your insurance’s subsidized rates. If you don’t have refills left, call your doctor and explain the situation. Many will be understanding, and so long as it’s not a controlled substance, will comply. While you’re at it, get your flu shot too. Stock up on birth control, or go through an online Canadian pharmacy. Get copies of all your scrips from your current doctors.
Do you have vision insurance? Compare your discounted prices for contact lenses with online shops, like vision direct dot com. Get a copy of your prescription from your optician - the reputable online contact lens sellers demand a real prescription.
Go to Planned Parenthood or a low cost clinic near you for your paps and gyno stuff. Investigate these now. The low-cost clinic will charge on a sliding scale and require proof of income - will you be receiving unemployment while you freelance? Bring that in as proof. Low cost clinics typically have long waits - try and schedule these appointments now for well into the future.
Get yourself a plan in place. Do you have any of those Urgent Care centers near you, like MedExpress? Get their phone number and hours and have them on a small card or stored in your cell phone. They set broken bones and do nearly everything. They should be who you go to in a small emergency (like, slicing your finger while cooking, needing stitches, etc). Big emergencies, go to the ER. If you make too much to go to the low-cost clinic, or you don’t have one or it’s inconvenient, go to CVS’s MinuteClinic or Walgreens Take Care clinic for routine stuff, like a physical or an ear infection or strep throat. These visits are, IIRC, $60. You’re seen by a registered nurse or a physician’s assistant. They have prescription writing abilities. You walk right in. They, IMHO, are much better at providing primary care.
Then, if you do get sick, always ask for the cheapest drugs available. Go to a pharmacy that has free or $4/month prescriptions available, don’t hesitate to call around either.
Hope this helps. Good luck!