I'm coming to YNAB from something like seventeen years as an avid Quicken user, and there's one concept that's still not porting across well: "logical asset accounts," which I use to track things like reimbursable expenses and "IOU" agreements with my spouse.
My approach in Quicken matches my understanding of traditional double-entry accounting. I have an asset account called "Reimbursable Expenses," and if I were to buy dinner on a business trip using my checking account debit card, I want to represent that transaction not as me buying food against my "Dining" category, but rather as a debit against my checking account with a balanced credit to my "Reimbursable Expenses" account. If the meal cost $50, I should have $50 less in my checking account and $50 more in my "Reimbursable Expenses" account, so that my net worth suffers no change. Furthermore, if I want to go back later and audit how much I spent on dining out, I do not want this business trip dinner to show up, because I was effectively spending someone else's money, and that money was not mine for the taking toward any other purpose.
Quicken models categories and transfers as dichotomous; every transaction has a payee, and is assigned either to a category (including each split entry) or as a transfer against some other account. In that sense, categories are like lightweight accounts. By contrast, YNAB models payees and transfers as dichotomous; every transaction either has a payee or is a transfer to another account. In the transfer case, YNAB considers categories to be ignorable, and the UI encourages (if not forces) one to ignore categories for transfers.
At present in YNAB, I have defined a "Reimbursable Expenses" asset account which is off-budget. The problem comes when entering transactions that interact with it: the payee is lost. Note that I see the same problem arise in the YNAB documentation for making a payment to a credit card company, but I don't consider that case to be as egregious. Say that I wish to enter a restaurant transaction against my checking account. If I cite the payee as "Fancy Place," I cannot enter the transaction as a credit against my "Reimbursable Expenses" account. Strangely, though, if I split the transaction, then I can enter some split entries as being transfers to the "Reimbursable Expenses" account, though in the latter case, since the "Reimbursable Expenses" account is off-budget, I'm then encouraged to enter a category, when I don't see which one would apply here.
Looking then at things from the "Reimbursable Expenses" account side, the register never indicates any of the original payees; every transaction is a transfer against some other account, so I can't tell, say, which restaurant was related to the aforementioned $50 credit. (Quicken could mitigate this problem somewhat because it's possible to right-click on any transfer register entry and select "Go to matching transfer," which navigates focus to the other side of the transfer in the other account's register. There's a feature request lurking there.)
It gets even worse: When I'm finally paid back by my company with a check, I want to enter that as a deposit to my checking account from the payee "My Employer" that credits my checking account for $50 and debits my "Reimbursable Expenses" account for $50, with no change in net worth. However, in order to enter the transaction as a transfer from my checking account to my "Reimbursable Expenses" account, I cannot enter a payee.
This makes me think that perhaps YNAB does not want me to model reimbursable expenses with an actual account. I can see creating a category for reimbursable expenses, which would allow the budget to react to funds leaving for pending reimbursement and returning later when the compensatory check from my company lands. However, this would then misrepresent my net worth. My checking account balance would be $50 lower after eating out on the business trip, but my net worth would also be $50 lower, even though an entity out there—my employer—is now carrying debt against me. We can argue that $50 is not a big enough deal to worry about, but I have accumulated pending reimbursements of several thousand dollars at times.
I mentioned "IOU" accounts as another variant. Say that my spouse forgot her credit card while we're at the mall, and I purchase an article of clothing for her, with the intention of her owing me the money back. We maintain an account in Quicken to represent this netherworld of such agreements. This clothing transaction would show me paying Nordstrom from my credit card account, but rather than the category being "clothing," it would be a transfer crediting my "Wife IOU" account. If I were to try to do the same thing in YNAB, I would lose the payee, and there would be no record of Nordstrom having been involved (a note in the "memo" field notwithstanding). That too makes me think that this approach is not how YNAB wants to work.
I'm interested to hear opinions on how to best model this reimbursable credit and debit flow in YNAB. Am I cutting against the grain here?