I also was buying out of pocket while employed for awhile. Unless you have a qualifying event you can only switch insurance at the beginning of the year, at least from the insurance options I was able to find that fit my family.

I honestly didn't even realize the thing about the standard deductible until I had already done it. I was shocked to find I couldn't deduct it because I'd have to use the itemized deduction which would have been lower. I just assumed my insurance could have been deducted like it was when I bought it through my employer... how wrong I was.

But yes I would absolutely prefer the "imagine if" scenario.