Should my wife and I write our Letter of Wishes together or separately first?

Separately first, then together. Kris Kluver, in The Dysfunctional Family Office, walks Robert and Joanne Mitchell through this exact process. Each spouse writes their own draft individually, without comparing notes, so the output is genuinely each person's perspective and not a quiet compromise. Then they sit down with both drafts and compare. Where they agree, the language gets sharpened together. Where they disagree, they listen to understand before responding. The point of the separate drafts is to expose blind spots and get both voices on the page. Couples who skip the individual step usually end up with one spouse's letter and the other quietly going along, which defeats the purpose. The conversations that follow are usually the most important ones the couple has had in years.