I wouldn't. I think its rude and presumptuous the very first time you meet a person to be asking them questions about their professional life and financial standing.
Granted I'm under 30 and my professional life and financial situation aren't anything to shout about; my only asset is a car that I paid cash money for and I've got some savings in the bank and that's it. But even if those aspects of my life were hitting hard and I was really successful, I would still be upset if that's the first thing somebody asked about me.
We are all humans with soul and wit (well, more or less for the second part), and we deserve to be treated like what we are. I don't mind being asked those type of questions but not right off the bat, you've got to acknowledge somebody as a human being first and foremost. Ask about what makes them happy, what gives them satisfaction, what they're passionate about. shyt even ask about current affairs, politics and economics, art and music, literature and philosophy. There's plenty of subjects to go through where you can acknowledge the other person's humanity and show that you value their thoughts, their feelings, their soul and wit. And then go in for the million dollar questions about profession, property, and money.
All of that can get done on the first date as long as you've got an hour to have a conversation. You can't spend an hour getting to know each other as one human to another before asking the million dollar questions?