Since I do okay, I'm not really concerned about his prospects or ambition.
Ambition usually translates into long hours at work, stress, and other boring things.
If he were a financial derelict I'd have to be prudent to shield my own assets from him, but I'm not looking for a meal-ticket or a sugar daddy at the moment.
If we clicked, we click and I'd be willing to see where it goes; I'd hate to pass on that "one true thing" because he wasn't even meeting his company's 401K match.
Here's a pro-tip for you OP - you put out slop and you'll attract the hogs.
Were I male, and high net or soon to be high net, I'd drive a non-descript car 3 year old car, wear a Timex or EcoDrive (very nice watches by the way), and live in a modest rental. Any women that had any problem whatsoever with that can self-select themselves away from you and save you the hassle, the time, and danger of trying to ferret out the more mercenary ones.
The richer I was, the shittier beater I'd have for day to day driving...
Don't worry about modding your life to appeal to women since you're actually modding to appeal to a certain kind of woman. And if you structure your life thusly and you then come to hate corporate law and paying 5K per month in mortgage and insurance payments ... you're stuck. Locked in. Another 20 years of grey death because you became what a segment of a population thought they were attracted to. And she's probably miserable too.
Look around at the grey men in the city, going through their motions, silently waiting to embrace the liberation of the grave. Or divorce.
Do whatever you want and live authentically and don't worry about meeting some theoretical female's checklist. Do what you enjoy without apology - confidence is sexy - and if a woman busts your balls on your lack of ambition just laugh it off. If she's busting your balls, she's interested in you...so roll with it.
If you do what makes you happy in life with no concern for being another tax/divorce machine mule, two things will automatically occur:
You'll be happy in your life - and that's no small thing these days, and
You'll attract a woman that is interested in you and not how much status, free cash-flow, or gala events you can get her into.
You're a man, not a mule or a a performing monkey. So live your life the way you want, unapologetically. The rest, including romance, will sort itself out with remarkable simplicity.