Legal Question in Tax Law in New York

These are very good questions. However the question about the LLC cannot be answered because the description of your current situation is contradictory as a sole proprietorship, by definition, cannot be a limited liability entity.

As far as employment, whether one is an employee or a freelancer is determined according to the job functions. New York state has been cracking down on employers that misclassify workers as freelancers instead of employees, as such misclassification denies New York certain employment taxes that otherwise would be paid. Whether you should be classified as a freelancer instead of an employee depends on your specific job functions and this needs to be reviewed together with you.

Therefore, unfortunately your good questions cannot be answered without reviewing your specific situation, job functions and what entities you may have formed. Such a review would take less than an hour and I offer lawguru users a discounted flat fee of $199 for such a review. At the end of the review your situation will be a lot clearer.

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Those are great very serious questions and the answers are more detailed than I'd be willing to answer for free via the internet. This really isn't the forum to get answers to complex questions like those.

Good luck.