I agree with PP that suddenly in this thread it feels like you are really processing some things and getting a bit angry about some of them which is HUGE progress. Previously I have felt the anxious love radiating off the page almost as if you analysing your DD's own behaviour would drive her off in itself.
That's not a criticism because I am really in awe of your steadfast good faith in all of this. I do agree that some therapy would really help you discuss and process everything that's gone on. Though I think your counsellor really, really should not be telling you her problems - to me that is a crossing of boundaries that is inappropriate in the setting no matter how much you like and trust her. I have had similar in a therapeutic relationship - partially my fault because I almost 'charmed' us into blurred lines - but i stepped away from that therapist once I realised 'hang on - surely this isn't right!'
I have had a few therapists to deal with family issues over the years and I think going to the occasional different one can be liberating (I mean not because chopping and changing, just because there were years in between the therapists) and it was ultimately a course I had over some minor issues that was so unbelievably... well, therapeutic and calming and freeing because I finally accepted who everyone else was and their limitations and who I was and my limitations and so I was able to meet people in a different psychological space and it was very calming for everyone!
As in, if you got to a place where you could be 'I love you, I don't agree with all of your choices and I refuse to say that I do, but I wish all of you nothing but the best with the outcome of those choices' or 'I love you, but I have nothing left to spend on you as I worry our relationship could be transactional, but I still care about you and want to be in touch with you' then I think that could bring you a lot of serenity and emotional freedom. You cannot staunch the wounds with cashmere and nice candles and creams and boots and posh pyjamas and designer kids clothes and sheepskin slippers and ranges and cows. You can't staunch those wounds with any material goods at all, but if you continue to try to then you will always be open to opportunistic and avaricious people who will take advantage of you and you will always end up being hurt. Whereas if you could accept that you have done and given a lot and that they have a lot, then you won't be leaving yourself open to these broadsides big and small.
You have been wonderfully generous and kind to ALL of your daughters, but I also think that as they enter 'real adulthood' of their thirties, things can and should change. I often think children of affluent families can experience a bit of kidulthood in their twenties as realistically there is always a safety net there and a cushion protecting against life's hard knocks. Which is lovely, but personally some of the big hard knocks are the things in retrospect have made me grow and have the most self-respect for myself!.
I have seen with friends whose parents have automatically met the bills for weddings and career changes and childcare and schoolfees that sometimes it's like a little bit of them hasn't really developed, because they don't have to really, really think about stuff? But as a kind and generous mother, you should be able to give them the pride and dignity and develop the thoughtfulness to take YOU out to dinner, or a play or a concert, because if you don't in a way you're depriving them of an ability to properly grow up. It is such a pleasure to plan for and treat a beloved parent. So that advice is for ALL of your kids. But I also understand that having worked hard and come to a comfortable place, you want to help the next generations - of course. But it's okay to not meet every single need every time.
Really thinking of you, and thank you for continuing to share this as it is so thought-provoking and illuminating about human nature and I think many of us really have thought about you a lot.
BTW I am the pp who suggested they are inspired by some of the homesteading christian US blogs. Interestingly in those there is a HUGE emphasis on supporting and respecting mom and dad and intergenerational relationships and the fifth commandment. So let's see if any of that seeps in!
FINALLY on this epic post, I was just reading a fabulous escapist saga by the wonderful Susan Howatch - The Wheel of Fortune. I don't think it's her best, but the principle she expounds in it, is that life is like a wheel of fortune, always moving away or towards ones ends, or like a spiral where the relationship sometimes feels like it is moving irrevocably away, was very apt for you. You're spiralling away from her at the moment, but it's okay, because it's really quite likely you will spiral back towards her - and be in a slightly different place, but closer.