To answer your first question, no, most schools will not superscore between the old and new SAT. The tests are too different for colleges to feel comfortable grouping them together for superscoring. Check out the answer to this other similar question for more details. You can also read this article that lists the policies of schools that superscore the SAT, including how they approach new SAT scores.
As for your second question, colleges will consider whichever score is highest according to the concordance tables published by the College Board. According to the tables, a 1400 on the new SAT is actually equivalent to a 1990 on the old SAT. There's no preference for a score from one test over the other.
I wouldn't worry too much about your essay score on the SAT (though keep in mind that on the new test the scores are out of 24 rather than 12! I assume you meant an 8-9 on the old scoring scale.). Since this version of the essay is so new, colleges will not consider it as strongly in their admissions decisions. It's definitely less important than SAT Subject Tests for schools that require those as a part of your application. Superscoring doesn't technically apply to the essay, but if you send in multiple score reports, colleges will tend to focus on your highest essay score.