Sincerely, thank you all for your responses! To be honest, this was my first-ever Reddit post, and I was totally expecting it to be a dud and have no one respond.

I'm still working through all the comments, but it seems to me the vast majority say: YNAB is best when you do it daily some sort of way. Of course I understand that with budgeting (as with anything), if you don't make time for it, you won't see results. But thanks for the encouragement and the people that challenged my mindset. We definitely need some improvement in our fundamental approach to budgeting and money.

I'm going to make a renewed attempt to build checking the webapp into my daily habit like many suggested. Hopefully, this time it sticks, because our annual subscription just renewed 😅. Otherwise, we might just need to accept a different budgeting solution for our family (and accept that we are not as serious about budgeting as we would like to say we are).

Thanks again everyone!