I had to put so much time (pre and once marriage) into earning money,

Lou,
I understand this feeling completely. It is very important to be a good provider.
But I am interested in your use of the word "had to".
I find many men neglect QT because " I was so busy....."
which leads to ignoring her need for QT. QT -in my opinion- shows interest and desire in the SO. Something everyone craves. There are so many things we put before our marriages/spouse. It end up being a Good Intentions road. However when he/she walks and suddenly we find ourselves with the ability to put everything in second place to the SO.
Also when we get the time, (hmm time, it just magically appears....) and or realize the need for it, the SO resists that QT. Why? Resentment- creating a desire to punish in kind, fear of the warm fuzzies that it generates because the warm fuzzies creates intimacy and may suddenly be yanked away again like it was in the past, leaving them vulnerable and dangling yet again.

Despite requests/statement of need for it. They Avoid the good, to prevent the possibility of hurt.

Make sense?

This fear of the warm fuzzies is one reason its so important to not personalize, and to ignore and plow ahead against any 'protests' about something that they do need.
An example of personalizing....

BF: <thinking -we need QT> Do you want to go to dinner at....
her: um, well, Im kinda tired....
BF: <thinking she doesnt want to spend time with me> FINE. just forget it then. <sulk away and pout.>

What have I just done? Given her a negative emotion. extract one credit from the LB. She is relieved now because dinner would have just been more of the same.

alternate progression.

BF: Im hungry. I want a steak. Lets go to.....
her: um well, Im kinda tired...
BF: <ignoring and plowing> yeah, me too. Lets get going so we can get back early. after a couple glasses of wine your going to be all over me anyways. <Confidantly throwing in some mental imagary.>
her: Ok.
BF: fix your hair so we can go. Just cause your tired doesnt mean I want to be seen with the living dead.
her: <hits me> jerk. <goes to fix hair>
BF: <watching ass wiggle away knowing, yeah, but you love me anyways.>

ok thats easy and simplified. after a long time of entrenchment and protecting themselves, you have to ignore and plow harder sometimes to the point of arguments, AKA rattling the cage.

The confrontation is necessary to get back to Intimacy.
It can not be avoided.
There is no easy button.
Its our biological imperitive/job to lead the way.

None of this was specifically about orgasms or faking.
Honestly, IMO, the power struggles have to be resolved in most SSM, before its time to worry about whether she is faking or you are a good lover.
Doesnt sound like faking is much of an issue in your sitch anyways OG.

About Oing.
When guys realize that a woman Oing isnt all that important and take off the pressure for her to PERFORM and expect her to think/approach/react to sex like we do then that will allow her to open up about it.
Womens sex drives are kicked in by her feelings.
Here are two things that dont work
Talking her to death about your sexual need.
catering to her every whim, following her around like a puppy, and in general vibing her with desperation for validation.
Oh yeah another.
projecting an attitude that "you owe me." That was mine during our reconciliation. < whack to self--ouch.>

A statement like BF #2 when the W did have an "O" how ever small or intense, is just asking for trouble

Yes it is. better be really damn sure of yourself.

What do you think of 'There is no need to fake an O. I would rather have the truth. It is easier to work with.

GREAT conversation starter. I like it. you have to show proof of words with actions though, and that means taking off the pressure for her to O. She isnt a science experiment or a engine to go examining or roughly poking and prodding around in despite Chrissys bad example to the contrary.
(sheesh woman, cut your nails, and make sure there smooth. you dont fool me dissembler)

If HairDog said the second quote to his W what do you think would happen
My guess is HD mostly knows what he is doing in bed. If he wants to send me a video, Ill peruse it and offer suggestions.
Ill also presume that his W is fine with getting her own. They need to have some knock down drag outs, but not about this.

I am posting the above because I am coming from a position of lack of success

Its all about perspective. I dont consider myself succesful either. I envy you your succesful 30 year, marriage, with grown children and secure retirement.

You had/have really good boundaries with your money management. BB liked that undoubtedly. Time to transfer those boundaries to another area of your life. Its really hard to get out of those entrenched nueral pathways especially when they are feed by early negative emotional motivators.

Take the dogs to the kennel, Drag BB along with you on some new adventures, and have some fun with her. Shake things up. Be unpredictable.