Suggestion - set up a “savings or money market” account in the same bank where your checking account/bil paying account is. Let’s say your annual insurance bill is $1200. Set up a $100/month “expense” for your Insurance Category. Transfer/Spend $100 each month from your checking to Savings/Money Market account (some banks let you set an auto transfer on a set date each month). That way it looks like you “spent” $100 each month. When your bill comes due Transfer the money into your checking account and allocate to your Insurance Category (don’t do the transfer out of the $100 on the month the bill is due). Pay the bill and it looks like you spend $100 for the month the bill was due because you only transferred in $1100 the month the bill was due. You could set this up for every “non monthly” bill (keep in mind you could do one transfer to Savings/MM each month that covers multiple non monthly bills and then split the “spend” across Categories). Yes a bit of a hassle and perhaps messes up some reporting depending on how you like to see things but it’s a way to at least allocate your spending on a per month basis and have the cash available when you need it. Plus you get a smidge more interest on your free cash flow (yeah not worth much now a days for sure)!
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