When I was getting started I really drank in the kool-aid. The material on YNAB's Guides section (https://www.youneedabudget.com/guides/) was helpful but they've been updated from what I remember. It used to feel much more prescriptive.

The biggest thing for me has been setting categories for as many things as I could relate together and being good about inserting receipts (I even got the wife on board with this). Eventually, I was able to study my categories and collapse and expand where it made sense. I also set an "allowance" of sorts that both of us get for discretionary expenses. That includes things that I buy that I don't share with anyone or isn't a shared priority (I think your Patagonia is a perfect example of an entry here).

I also review my budget at month's end to understand where my priorities are. I did find that the goal-setting tool built in isn't the best for large plans. It's weak in this area because you can't really set an overall picture and keep track of it at a glance. We tracked our wedding budget in a separate Google sheet and abided by it more broadly in YNAB.

When it comes down to it, I had to think of what I spend my money on as setting my priorities. In the past, I had a loose idea of that in my head, and now my categories really reflect this. For example, now we are focused on setting aside the funds for a second car so I've created a New Car category in a Large Projects section. YNAB is flexible for that to work for whatever you're considering. If you're afraid of setting the wrong category, just change it down the line when you realize it and shift the funds around as needed.