I used to use YNAB before it was a "web app", and it was pretty auto-pilot after setting up the imports/rules. It classified 98%+ of all my expenses and inter-account transfers without any issue. Every once in a while you had to classify a new transaction but that was rare after a while. Anyways, the ones that are rare like that are usually once-offs and you're already making notes next to them so you know what it was for.
Maybe I'm misunderstanding something, but I've watched several tutorials... The workflow seems to be: Every time you get paid, you go in and assign your money to your budget. This is the "make every dollar work for you" part. But that involves going to each non-green line item and adding some amount of your remaining money to that item.
It doesn't really have an idea of when expenses are due (though you can set up dates on goals, but multiple tutorials I watched recommended putting the due date in the name, so you can manually sort the items. It also doesn't have an idea of when you get paid. So it can't do things like: "You're going to need to pay your mortgage of $X in 2 pay periods, so let's allocate $X/2 of this paycheck to the mortgage expense.
In fact, it doesn't support even "add the remaining amount for this expense", so you're going around typing the dollar values of different expenses.
I understand that this is part of their design to get people more familiar with their money and where it's going. Maybe if I was waaaay off track, and really pressed for money, that would be valuable. But I'm 90% on track, my worries are kind of higher level.
Again, maybe I'm misunderstanding something. But I've watched hours worth of tutorials, by YNAB and others, so I've at least done some level of research. :-)
I think they went a little too-heavy into the "manual" part of YNAB at some point. Internally and from the UI (YNAB 4) it has everything to do the stuff automatically and that's what I do.
E.g. When I get paid, that gets loaded into YNAB using a bank-import. So even if the rules don't run, I just have to go through all my "transactions" that got loaded from the bank import and just assign to pre-defined "payees". Further, each payee has a linked category so I don't have to categorize what expense that transaction was for, because it's implied by who the payee is. E.g. A butchery store payee means the category is e.g. "Groceries - Food - Meat" or just "Monthly Groceries". YNAB also has a filter where it highlights all transactions that haven't been assigned.
With the above stuff, there is no need to do any manual or scheduled expenses. The only time that doesn't apply is when you withdraw cash and spend it that way. If you do a lot of cash transactions, you'd have to do that manually unfortunately. But for myself, what little I spend using cash I just zero-out my "cash" account every once in a while with a manual transaction that is an "unknown expenses" budget category.
Some of the stuff above is specific to the YNAB 4 desktop software - before they converted to a subscription web-based tool.
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.
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.
