[joshstrange]

Goals are going to be your friend here. I have goals on all but 1-2 categories (categories that I rarely contribute to or are just holding the money, like my taxes for freelance work) and I can select all my categories and auto-fund them all in like 3 clicks. That's pretty much all I do on pay day, go out to the furthest month I want to budget in advance, select all category groups (or most if I don't have enough money for all) and click "Underfunded" which will put the right amount to cover my goal for the month. If you set up recurring transactions the "Underfunded" button will fund it exactly what it needs. I almost never enter numbers manually. It took me 2-3 months to get my goals dialed in because I started with guesses and went from there and sometimes I still find myself saying "Ok, I'm always pressed on this category and it's more important to me than X so I'll start funding it more going forward".

You are correct that it doesn't have a concept of when you get paid or when your expenses are due, though I set up recurring transactions for everything, even things like utilities that fluctuate. I just go in on the first of the month and adjust the pending transaction to be the correct amount for my electric/water/sewage and save it. The whole idea of not telling YNAB how much I make a month was very confusing to me at the start coming from tools like Mint but there is a method to the "madness". For YNAB you never count on future earnings, all you can spend is what you have at this point in time. For the first month or two you might not finish funding the current month until part way through it but the goal is to get 1+ months ahead on all your spending so that you are always spending last month's money instead of living paycheck to paycheck.

Here is the video that helped me the most when I first got started, maybe it will help you as well: https://www.youtube.com/watch?v=xPVEB759gkU

I tried YNAB4 (app-based) and nYNAB (web-based) both once before the most recent time I tried YNAB (starting May 2020) and this last time was the only time it "clicked" for me (and the first time I really got serious about my finances). YNAB has been literally life changing for me. I went from living with a very small buffer (despite my well-paying job) to having 3 months in the future fully funded. The peace I mind I get from knowing I could lose my job tomorrow and be fine for 3 months minimum (I'd probably cut some categories and/or plunder some savings-based categories to stretch it longer) is amazing. My bank account has never had this much money in it in my life and despite having to take a 20% pay cut for about 6 months, due to the pandemic, I stayed on track for everything and continued to grow my net worth.

I know I probably sound a bit like a fanatic or a "true believer" but YNAB (once it clicked for me) changed how I interact with money and my finances as a whole. I really hope it works for you or you find a tool that clicks for you if it's not YNAB!

I'm happy to answer any other questions you might have on it. I'm forever grateful to the friend who nudged me to try YNAB again and I feel obligated to "pay it forward" whenever I can to help other people get started on it.