My stance on this is if you're going to delay paying, make it count, and make sure there are no/low penalties for screwing up. I only delay paying local taxes until the due date, or a bit later if it slips my mind. Here, sole proprietors get the entire year's local tax bill at once, with the option to pay in full or in four installments spread over seven months. In the past, I took the former option, mainly to feel free of it. I stopped doing that, and paying social health and national pension premiums up front for a 1% discount, after learning about FIRE.