If you lost your wife several yrs ago (mine fears her cancer will come back after 8 yrs), then your heart may be just ready to open its bud again, and the chemistry (measurable thru astrological composite charts, if it's a factor) plus the obstacles are enough fertilizer for your heart. Would she be switching from one sugar-daddy (who she's bored with) to a new one (with greener-thumb chemistry)? Life can be a bed of roses if you're a queen by marriage whose husband's kingdom supports your throne, so you (like Princess Di) can devote your energies to benevolent support for others. That is an upperclass ideal few contemporary American women get to live out. But does your financial power make you such a king? Wouldn't other (younger, if you prefer) women want that role too?
What "Princess Di" offers in the modern marriage (discussion type in my textbook) is Romance. Sounds like she might be good at that; but what else does she want to make HER OWN LIFE meaningful--besides practicing benevolence?
What do YOU want in a partner & a partnership? Which types of spousal Intimacy were most meaningful in your former marriage? And which do you yearn for now? (You can use numbers for degrees of importance: 1 = mild 3 = maximal)
Types of Intimacy [From Love & Intimate Relationships: Journeys of the Heart, Brown & Amatea, 2000.]
1. Physical. Familiarity & closeness with another's body in work & play, medical care, touch, massage.
2. Sexual. Erotic pleasure sharing.(The typical default meaning for men, whether verbal or emotional sharing are involved or not.)
3. Emotional. Empathic attunement & expressing emotions. (The typical meaning for women, though the reality may be that one is giving & receiving only the emotions one wants, and not Crisis (9) or Conflict (10).)
4. Intellectual. Sharing spheres of ideas.
5. Aesthetic. Sharing experiences of beauty and excellence.
6. Creative. Sharing acts of creation together, including brainstorming.
7. Recreation. Fun, sports, play.
8. Work. Cooperating in tasks or occupation, wage-earning.
9. Crisis. Facing crises, problems & pain together.
10. Conflict. Struggling with differences & frustrating interaction cycles.
11. Commitment. Trust & mutuality from common investment of self.
12. Spiritual. Sharing religious, spiritual & transpersonal experiences & concerns.
13. Communication. Verbal sharing and understanding. (Typically combined with Emotional, Intellectual, Crisis, Conflict, etc.)
Have you been looking to replace the types of Intimacy you lost when your wife died? Or has your advancing age (& maturity), plus perhaps a transformation through a widower's romance led you to seek different core intimacies that what your habits had been?
If Judy has a hold on you, it's possible that you could experience a melt-down of your identity-up-to-now and a subsequent rebirth as a new man, even if Judy isn't loving you in the same ways as you're loving her, and even if the romance doesn't eventually restore the stable partnership you might be seeking (ie "Commitment" intimacy).
However, if you don't feel respect for Judy's handling of money, you'll be feeding the thorns of your relational destruction if you-or-she don't face it & change.
I think you're asking me to rain on your heart's party. But fear of deepening investment of self (aka Love-development&transformation) is right on-time at 4 months.
I'd be uneasy about approaching her husband, worried that hearing his history with her and possibly jaundiced perspective would turn your rosecolored glasses yellow, OR that he'd gladly "give away the bride" which reinforces his hold over her and demasculinizes you. I sure respect your confusion.