Welcome!!! You'll find this community to be wonderfully supportive.

As for the cash question, if I read the replies correctly, I do it a hair bit different. Just another option for you to think about.

When I withdraw from the ATM and spend it all in one transaction, I do NOT categorize it as cash. Example, I took out $20 for fresh produce at the farmer's market and spend it all. My ING account online shows a $20 ATM withdrawal, BUT my YNAB checking register shows the category as Food: Groceries and $20 outflow.
If I withdraw and only use SOME of the money (whether on a few transactions or one), I will do a split transaction in my checking register. I will categorize the spending I did and then with the leftover cash, it will be a Transfer-->Cash with the balance and no category indicated. A perfect example of this was Saturday. My DD7 had a cheer competition. I knew I needed cash for parking & the tickets to watch. I also knew we weren't supposed to bring outside food in. I took out $100 at the atm. Ended up spending $12 on parking, $15 on tickets, and *gulp* $19 on a couple snacks (crazy expensive there!!). I lumped it all as one line on my split transaction (dear hubby so graciously said it could come out of his fun money.) On the way home, we picked up pizza. I paid cash for that and indicated that on another line in the split under Food: Restaurants. After the day was over, I had $21.76 in cash. That was a third line in the split, where I transferred it to our Cash account (and now when I use it, I'll enter the transaction in the Cash account.)
Hope I've helped and not confused!
