I've recently (3 months ago as of writing this) got into proper double entry bookkeeping for my personal finances. I've been using GnuCash, though this pertains more to double entry practices than software specific.
My fiancé and I have just closed on a house. We did not pay in equally, and we want me to "pay back" the difference over time. This will be done through purchases for the home, utilities, whatever. We already have a similar setup where we balance out things like our groceries. We track our own food expenses, but we buy them on one transaction on the trip, balancing over time by taking turns paying.
The problem for me is that the whiteboard account is only a half solution. I track my actual expenses in GnuCash, but not theirs. So when I owe say $10, and I pay for $10 of items for them along with $30 for myself, the entry looks like this:
This works as it tracks my total spend, the expense for my food, and reduces my owed amount on the board. So then I look at how my credit card works, which is Card credits to Groceries, and later Checking credits Card. But with that account the debt is created as needed and temporarily. With the house repayment I have the debt all up front.
So the question is, how can I track the flow of money from Checking, have it pay down the existing House Repayment debt, and also have the dollar amount tracked in House Expenses? Essentially the goal is that at a certain point in GnuCash my transaction report totals will balance and I will have put in as much money as my partner, and we can then move to a new balancing system.