Planning ahead with YNAB
How far ahead should I budget for anticipated future expenses? I just mean regular things like rent and utilities. I can see that budgeting in future months is an option, but it's not clear to me how to use it.
It depends but generally, it's a pain to budget in the future as it means a lot of flipping through screens if something changes. I don't budget in the future. I budget the same amount every month for each of my true expenses. Everything I don't need to budget for this month expenses or to build up funds for known future expenses is budgeted first towards unknown future expenses (car repairs, home repairs...) then towards savings (new furniture, new car, vacations etc.)
I try to budget the same amount in all categories every month so budgeting is a very simple process. I make some changes from time to time especially when changing saving goals or if some repairs have depleted a repair fund and I want to build it back up faster.
The long-times users around here will tell you to abide by the old Classic YNAB Rule 4. Live on last Month's Income. That means budget October with all income from September, November with all income from October, etc. No further. The idea is to get away from budgeting with every paycheck, because you will actually look at your budget differently when you can budget for the entire month, as opposed to having to decide what to do with every single income event throughout the month.
Then figure out how many months of cushion you want, multiply your income by that number, and store it in a category called Emergency fund or Income Replacement.