Just responding to the specific example, I've been very happy with square / square wallet in this regard. The system recognizes my card, and offers to send me

Just responding to the specific example, I've been very happy with square / square wallet in this regard. The system recognizes my card, and offers to send me an itemized receipt via email for any transaction. I can use this to clearly see the merchant, date/time, and what I paid for. Simple (the bank) is making inroads in this as well, and even PayPal's receipt emails are more descriptive. Maybe a bit too complex of an issue for a startup to hit now (look at what happened to Dwolla) but certainly still a lot of "pain points" to solve left.