The issue with both of these approaches is that companies share data, so at the end of the day all the companies (and the glowies) know everything about you.
However, you can use encryption, alias emails, and FOSS services to minimise the number of parties you trust, while also giving them the bare minimum amount of information needed for what you want to do.
edit: Approach #2 might work if you don’t have any common indicators between accounts, but that’s highly impractical at best (assuming you’re using shady services).