Does a high superscore mean less than a high single score?

There are two parts to that answer.

First, there are schools that do not superscore. To those schools, you have a 1390, which would obviously not be as competitive as another applicant with a 1440 single sitting, which means a 1440.

Then there are schools that superscore. According to what they say, both 1440s are exactly the same. Do they subconsciously note the difference? Do they even see that it’s a superscore? Who knows. Everything schools publish and say, they’re the same.

Unless you know all the schools you’re applying to, there’s a chance some will be single score. You’ve shown the capability for both scores, it’s still early in HS, you have time to prep, and three sittings isn’t overkill. If you have time to properly prepare, I’d suggest one more try in the Spring.