@C_Heath-Veik
The best way to record this is to create four separate Expense transactions (New > Expense), one for each of Jan. - Apr. On each expense transaction, enter the health insurance provider as the Payee, enter a line item for the monthly health insurance cost as a positive amount, and enter a second line item as Partner Draw as a negative amount so the transaction nets to $0. If you keep separate partner draw equity accounts, add separate line items for you and your wife's portion of the expense. If you don't keep separate partner equity account, just enter it as one line item as previously mentioned. That will increase the partnership health insurance expense as well as your partner equity account(s) for the amount of the health insurance paid personally. There's no need to transfer cash into the business.
