I love that you suggested YNAB here but I have one significant problem with it that doesn't have a consistently good workaround.
Reimbursements.
When I m out with friends and the restaurant doesn't split the bill I'll often cover it then get paid back with cash or PayPal. YNAB doesn't seem to handle this very well.
Then wirh longer term reimbursements it gets worse. Either you forget that you are owed or you float the debt.
I still recommend YNAB. but that specific problem means it's not on my "reliable" list.
Split the transaction in YNAB, send your part to the correct category "Dining", and itemize owed amounts per person into another category "Loaned Money". It's easy to track if "Loaned Money" has a positive balance, and you don't screw up the budget for your Dining category.
Reimbursements.
When I m out with friends and the restaurant doesn't split the bill I'll often cover it then get paid back with cash or PayPal. YNAB doesn't seem to handle this very well.
Then wirh longer term reimbursements it gets worse. Either you forget that you are owed or you float the debt.
I still recommend YNAB. but that specific problem means it's not on my "reliable" list.