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Hey @ryleibel
1. As per CFA work guidelines, any job that you can reasonably interpret as contributing to investment decisions (whether they are investments in securities, or investments in projects undertaken by your company) will work. Depending on your role in insurance, that may qualify as well.
2. Schweser’s a pretty popular provider, so don’t think you’ll go wrong there. I haven’t used it myself but the blog has tons of advice. Just follow it, and read the archives!