@ndjohnson8 

I'm not sure your accounting background but the best way to handle these transactions is to create a journal entry each month that debits Insurance Expense and credits Accrued Expenses (liability) for the monthly premium.  Then, when the bill arrives, list Accrued Expenses as your account (category).  That will book one expense entry each month and the bill will reduce the accrued expense liability.  That way, you can enter one bill (if billed for multiple months) and the date of the invoice is irrelevant on your statement of activities because the bill only hits balance sheet accounts and not your statement of activities.  The multiple bill option works but if you're comfortable with journal entries, this way is the proper way to do it.