Can I afford to take this job's high-deductible health care plan?

First some numbers for 2021 from the IRS:

Annual contribution limitation. For calendar year 2021, the annual limitation on deductions under § 223(b)(2)(A) for an individual with self-only coverage under a high deductible health plan is $3,600. For calendar year 2021, the annual limitation on deductions under § 223(b)(2)(B) for an individual with family coverage under a high deductible health plan is $7,200.

High deductible health plan. For calendar year 2021, a “high deductible health plan” is defined under § 223(c)(2)(A) as a health plan with an annual deductible that is not less than $1,400 for self-only coverage or $2,800 for family coverage, and the annual out-of-pocket expenses (deductibles, co-payments, and other amounts, but not premiums) do not exceed $7,000 for self-only coverage or $14,000 for family coverage.

Focusing just on the family plan numbers:

• Deductible $2,800 or higher
• Maximum out of pocket $14,000 or less
• Maximum amount you can put into the HSA $7,200

Here is some info from your question:

• However, they pay the premiums 100%, so I would be putting the money I spend on premiums for my family into this.
• I currently spend $159.50 twice a month on insurance premiums for medical.
• In addition, I spend 114.58 twice a month to fund my FSA, which is capped out at $2700 and which we usually spend most if not all of in a given year.

So looking at your current spending: of $274.08 twice a month, or $6,577.92 per year. That means that you can almost completely fund the HSA with the same money you were spending on the premium and the Flex Spending account. Just like your old plan this will be 100% pre-tax, without the use or lose risk.

You will need to know what happens between $2,800 and $14,000. In the plans I have had access to it has been 20% paid by the employee and 80% paid for by the plan. You should be given this information with or after the offer letter. Please ask for this detail.

If prescriptions coverage is important look to see what they charge for prescriptions before the deducible is met. You shouldn't have to pay full price.

Before the deductible is met you generally pay for everything except the procedures like a annual physical, and other items defined in the Affordable Care Act. But if you are going in-network even for those things you have to pay for, there should still be discounts due to the negotiated rates.

Whenever you are switching insurance providers, and sometimes even when switching plans within the same company, make sure you know if your current doctors and providers accept the new plan. Going out-of-network can be much more expensive in this type of plan.

This answer has completely ignored dental and vision coverage, because it wasn't mentioned in the question. They may have separate premiums, and in your case they are hopefully 100% paid for by the company.

Due to adverse selection the HDHP is almost certainly the better deal. When HDHPs were new the healthy went with them and the unhealthy went with the traditional plans. Insurance companies learned this and have set the premiums accordingly--the additional premiums for the lower-deductible plan are usually similar to the difference in the maximum out of pocket.

If you don't meet the traditional deductible you're clearly paying more for the low deductible plan.

The stop loss is pretty much fixed, if you reach it you again are clearly paying more for the low deductible plan.

This leaves only the range between the low deductible and the stop loss where it's even worth considering. Add up the premium difference and add it to the deductible (it's money you're certainly going to be paying)--and in my experience you get numbers close to the high deductible plan. I've never seen more than a narrow window where the low deductible plan comes out ahead.