What is your primary purpose for Obsidian? (Note-taking, research, writing, project management, PKM)
What does your current note-taking system look like? What's working and what isn't?
Are you familiar with Markdown?
How much content will you be working with? (Dozens, thousands, tens of thousands of notes)
Do you need to sync across devices?
Will you publish any of your notes?
Are you comfortable installing community plugins?
What other tools do you need to integrate with? (Zotero, Readwise, Todoist)
Do you prefer structured organization (folders) or emergent organization (links and tags)?
How much setup time are you willing to invest?