The reason I would do it is because being stuck is depressing and getting to participate is fun.
One SP book, SP bundle of stories, or even one free SP story is just that, not a career. And it is much more fun than nothing. It is a start, if nothing else.
I think your writing is definitely good enough to be published but your problem is you won't go after publication
aggressively because the rejections get to you too much. I haven't checked duotrope lately but I believe I have about 600 rejections- I also have over a hundred acceptances. I don't care, so I send things out aggressively. I'm also not snooty about which publications I'll accept. While of course I would accept fame and/or fortune, my main goal by far is just that I want to be in the game in any capacity, I want to play. Perfectionism or impossible standards kills the fun for me. It's more like, catching the brass ring now and then is an extra kick for me, not the only kick.
I like the philosophy, "Do what you love and the money will follow." But I'd add, "Or else it won't follow but who cares because I am getting to do what I want to do."
The point, imo, would be to get
unstuck right now. Then worry about next time when next time comes around. Right now, I have been paid for some stories and articles, not paid for many more, and I make about $100 a month combined from my four short SP books. See, all that motivates me to keep going, and keeping going is how to improve and how to enjoy. Maybe I'll end up being a career writer (meaning making enough to fully support myself) and maybe I won't. But I have everything I need from other sources and it sounds like you do too, so just getting to do what you want to do is a giant privilege in itself, imo.
Just my opinion, naturally, but I am a very happy writer and apparently you are not (?). That would be my reason to suggest you try it my way. However, maybe just jumping into the game anywhere and going from there doesn't appeal to you, in which case of course it doesn't help. That's all I got. Good luck!
P.S. Husband and I plan to start keyboard (him) and guitar(me) lessons for the New Year, again to play and have fun, not as a job. But hey, if we ever ended up getting a paying gig in the far off future, we might take that, too. Bonus money is fun too but if I needed to make money and that was my main goal, I would go back to work. I'd rather have less money and get to write.
I would buy your book, so there's one sale anyway.
Publishers do seem to be doing that "no answer if they don't want it" thing more and more lately.
How about this (if you feel like answering), what is the easiest thing you could get that
you would consider a win? Like what type of publications, what type of pay. I just feel like you put too much on yourself when there are so many variables about what stories are chosen.
When we have all seen very many trade published things that were not good, why do you feel like they are the final arbiters of what is actually good or not? McDonald's sells more hamburgers than... well, tons of them. So is McDonald's the judge of what food is the best?