There's no way that's okay

Interesting, FreeTaxUSA didn't say anything. I'll have to crunch the numbers, but I think I can split the expense to claim part for each deduction, and still hit 7.5% together with medical bills.

NJ State tax also has a medical deduction, must hit certain thresholds too

Much lower I think 2.5%

I was wrong. They do mention it on the Schedule A page:

You've already reported $XYZ of health and long-term care insurance premiums as business expenses so don't include those here. $ABC of these business expenses couldn't be deducted from your self-employment income and will instead be included in your itemized deductions. Don't report these expenses again below.

Trying to figure out how to apply this info to my own scenario. Are healthshare contributions eligible? What about health expenses besides for premiums?

It sounds like just premiums, but it includes dental and vision. https://www.irs.gov/pub/irs-pdf/i1040gi.pdf Schedule 1 Line 17 (pg. 94)

You may be able to deduct the amount you paid for health insurance (which includes medical, dental, and vision insurance and qualified long-term care insurance) for yourself, your spouse, and your dependents.

insurance premiums from work were already paid pre-tax so that's not helpful, right?

Correct. This is for self-employment.