>The free plan's maximum out of pocket contribution is $8,700, which exceeds $7,500 I see as the $2023 number.
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>Is the $7,500 max out of pocket a cap or the threshold? Basically, will the play qualify as HDHP?

To count as an HSA eligible HDHP (using 2023's individual coverage thresholds), the plan's out-of-pocket maximum must be lower than $7500. There are also a couple other criteria for HSA eligibility: the plan deductible must be higher than $1500 and the plan cannot cover anything (other than preventative care) prior to meeting that deductible. So if the plan involves co-pays prior to deductible, it won't count as HSA eligible.

In practically all cases, if a plan is HSA eligible then it will say so. If that's not part of the description, it's almost never HSA eligible. So enrolling in that plan means that you would not be allowed to have an HSA, even one you opened independently. Ok, technically you can open one, but you're not eligible to contribute anything into it, which makes it effectively useless.

>If not, should I sign up for the company's FSA, even if it does not roll over unused funds?

Do you have any known (or at least high-likelihood) medical expenses for 2023? If so, then you can enroll in the FSA up to that dollar amount. Think of the tax savings of the FSA as a "discount" on your medical bills. You contribute, say, $1000 into the FSA but your take-home only goes down $800 or so. You can then use the FSA to pay for $1000 of medical costs, saving yourself $200. And that FSA money can be used for your expenses, your wife's, or dependents (if any), even when they're not covered by your insurance plan.

One benefit of an FSA vs. an HSA is that the full dollar amount is available to use immediately at the start of the plan year. You don't have to wait to "fill up" the account from your paycheck deductions. The biggest drawback is the FSA's "use it or lose it", though some will rollover some dollar amount into the next year. Or it'll have a grace period where you can use 2023 FSA dollars for expenses incurred during the first few months of 2024.