People are going to judge. It is human nature. Positive or negative, folks have opinions about what others do. I cannot imagine living your life, the dedication you have put into it. But I hope whatever you decide, you don't let others make you feel bad. You have done all you can and far more than most would ever have done.
Doing rescue, most of us rarely see your kind of dedication. I wish it were harder on some for whom getting rid of a pet is so easy. It's not just the US, take a look at even France, Germany and Italy and the stats on getting pets then putting out on the road at vacation time. Public media has helped, but how could anyone be okay with that? From getting new carpeting and the dog hair stands out to having a dog for 12 years but now having a baby and no time for the dog, to you name it. So no, I don't think giving up a dog is that hard for many people.
When someone wants to place a dog and is trying to do it responsibly, like the OP, then yes, we need to not judge. But I do think if someone posts on a public forum saying they are only trying to place the dog because of concern for the dog's happiness, then they should expect, in fact want, to be asked about options that would allow them to keep an older dog, because it is so hard on the animal and if they can be supported to find a way, then suggestions are not judging but trying to offer options. If the OP really is concerned about the dog's welfare, they can say the breeder is not an option, and suggestions won't work for their situation. Nothing was asked here that a responsible rescue won't also ask.
As for your situation, you make your own decisions about what is best. But it is heartbreaking that you suffer taking care of Oakley at such an expense to your own happiness. You need to take care of yourself too. (( Hugs ))