I agree. Life is a bit simpler for me being single and not having big recurring expenses (my only monthly bills are rent, phone, car insurance - and I'm getting rid of the car).

I think a tool to show behavior patterns in spending would be immensely helpful. I typically spent very differently when money was tight vs when my credit balances were at $0. It took me a few cycles before realizing that as soon as I had a couple grand in my pocket I'd make some big ticket purchase that wasn't always necessary. In fact, I'm fighting off the urge to buy a new rMBP right now! hah.

I think what you're talking about is a problem that nobody has even attempted to solve yet. I normally spend about $75 /yr on "financial tools" (usually credit reports, fico scores, etc), so yes, I would be willing to spend money on something like that if it were good and could learn & show my patterns over time.

Heck, if it sat watching my browser history and would ask me if I really wanted to buy X when I'm spending too much time looking at it on Amazon, that'd be killer! lol