1) What is motivating this change? Are you currently unemployed, looking for new work or rather concerned about ensuring your employability over time? Are you looking to earn a higher salary?
2) In an ideal world, would you want to learn this new technology or would you rather stick with building your existing skills / working with tools you are familiar with? Are you willing / interested in learning these tools outside of work, or would do you have other engagements that take precedence (family, non tech hobbies, etc).
3) How much risk are you willing tolerate? Do you have a big enough safety net if the independent contractor thing doesn't work? Maybe plan out this scenario on paper, and do some rough math if possible.
4) You are well within your right to avoid management roles (or anything that doesn't serve you). What are your goals with work, pay the bills even if the work is tedious, emotionally challenging?
My apologies if these questions aren't helpful for you. I'm just yet another obnoxious 20 something in tech.