Yes, you'll need to cover anything due before about the 18th, in case the 15th is a weekend.
If you have access to a computer, the web version is so much easier to do stuff on. I think there's an official way to make goals etc linked to a date, but I just put the date that monthly things are due in the category name, so it's like
💡 Electricity 22nd
🏠 Rent 1st
🎵 Spotify 15th
etc. I put them in order to make it more neat :D
I think according to the YNAB philosophy, the end goal is to cover all of November with that payday that you have in October, which you do by gradually covering just one more thing in the following month, each month. But you might want to focus on other goals first such as building up an emergency fund, funding "true expenses" (e.g. your yearly bills) - which are always harder when you first start because you're already part-way through the year - and paying down debts etc.
In total honesty I still have not got "a month ahead" - DH gets paid on 25th, so I cover 90% of the bills up to the 26th, plus the first 1-2 weeks of food shopping, using his pay, then we get child benefit - higher than UK - in on the 7th-10th (ish) so I cover the last couple of bills and the rest of the month's food budget with the child benefit, if there's not enough and the last Saturday is after the 26th, then I leave it until payday.
There is one big bill (€270 loan repayment) which comes out after DH's pay which I tend to just cover on payday that same month, rather than trying to cover it with the month before. I don't know if I will skip ahead with that one! It just feels like such a big chunk of money that is better used in the overdraft clearing or emergency fund. We have about 18 months left on it so we'll see I suppose.