I got confused about which "secret" you were considering sharing.
--Twiggy's trauma?
--the fact that you have considerable wealth?
I THINK you meant the latter, and agree, no need to spell it out unless/until you two are talking together about specific plans to join your lives, have him move to your mountain, etc. At or before that point, you just need to completely divorce it from notions of masculinity or femininity or ruggedness or power, and just present it in a matter-of-fact way that has no shade of entitlement. Money just what is. A fact. And a lovely one that enables you to enjoy your mountain plans, and would of course also enable you to take care of each other.
On the other hand, when I met M we were both specifically looking for commitment, and I let him know early I wasn't interested in being a "girlfriend" in this chapter, and he said he also saw marriage as the natural outcome. So since that was clear, I told him all about my finances (which fit on a napkin) almost immediately. I also mentioned on the 2nd or 3rd date, when his life stories made clear he had considerable wealth, that it was critical FOR ME that we have a prenup if we ever married. He was startled but appreciated it once I spelled out why (so noone, especially including his children, could ever fear I was in it for the wrong reasons).
I didn't learn the real amount of his assets until about 4 months in (I had just figured, from the family stories, houses in multiple, ambassadors, industrialists, etc). At that point I told him, "I could tell you right now what I'd ask for in a prenup--a bit to fix up my little house, which would be rented--and enough to live in a decent assisted living/continuing care facility so I wouldn't rot in a bad "home." He immediately said, would X be enough? Or Y? Those amounts were so stunning to me there was nothing more to say. It's clear he would take care of me fully. But I will still insist on the document, as we get closer to picking a date.
(It's taken me quite a while to internalize "will be taken care of" without fear of loss of independence, but M has consistently shown he wouldn't use it as malignant power over me. He does use male entitlement in an oblivious/intrusive way at times, but never uses his financial power as any sort of threat, only to enhance our lives together. I don't know how that might change if I were demented or ill, but I have legally protected myself against everything I can through the trust I have, plus the 5 Wishes document. The rest is personality stuff, and if I were too far gone to argue, I'm not sure my assertions of autonomy would be relevant -- or even possible -- then.
Buck is a different person so it might take him longer to absorb the difference in money between you. But it might be good not to fantasize too much Outlander into his psyche. Autonomy and independence are matters of respect more than power (money does equate to power to some degree, but it's all in whether it's weilded and how). I think you respect him so much that you would never even hint that if he accepts some support, that this has anything to do with his pure, core independent nature. And you're wise to hold off and tread very lightly. (I nearly broke things off with M because he waded in to "help" my D without understanding the sensitivity of the damage and even my ongoing acceptance of No Contact without my existence being acknowledged. For him to start reaching out to her or even vaguely have "a plan" to was an unbearable use of his reflexive entitlement.)
I think it might be good to tell him something that really benefitted me to tell M, if you find it fits. M was batting away my attempts to give him things, treat him occasionally on my own dime, etc. One evening I explained to him that because of my Dad's habit, when he refused to receive, he was actually hurting the giver's feelings. Giving is an opportunity to show gratitude and love, and when he insisted I mustn't give or spend anything on him (which he thought was kind and generous of him) he was actually depriving me of something important: the joy I feel when I can show appreciation. I told him how much that distressed me as a kid, when my self-effacing (to a fault) father would wave away so many of my attempts to show love through a gift or gesture and he'd respond, "No, no, I don't need anything." The moment wasn't about my DAD'S need to be self-effacing, it was about MY need to show love. And my sweet Dad never realized that. Not his fault, just learning.
I'm probably way off track because I find your descriptions of the issues a little bit opaque, but that may just be the positive habit of discretion and respect for everyone's privacy. For which I salute you! But we're anonymous here, and safe.
Hugs
Hops
