Thank you for candidly sharing your thoughts & experiences.

As a fellow bootstrapped entrepreneur (& programmer), I sympathize with what you're going through. Maybe it's the survivorship bias but I think you could try some things differently. I'm not sure you're open to receiving advice but I hope you find it at least well intentioned.

My biggest piece of advice is that only the sales channel really matters. People talk about product-market fit but that's kind of ambiguous. What you need to do is really understand some sales channel. Your real goal isn't to create the best product in the world, it's to own some sales channel for a particular category. Take movie theater food for example. It's shitty & expensive but keeps selling because it's the only thing available. It may even be helpful to ignore the actual product part and learn about understanding and identifying opportunities in sales channels first. Then you build the product to dominate that category.

Sales channels can be content marketing, google, facebook, amazon, trade shows, in person meetings, and more. For example, if you wanted to do content marketing. Instead of building a product and hoping that content marketing would work, you should learn about how content marketing actually works. Things like link building, content optimization, technical SEO, and keyword research. Then you could find categories you're interested and start seeing where the competitiveness is relatively low compared to the volume. You may also learn that content marketing usually takes 5-figure investments + months to work even in niche categories.

If you really understand a sales channel, the opportunities become obvious. Most people don't really understand why Gitlab succeeded or how it's different from Github. If you're running a dev ops team with a requirement for an on-prem OSS solution, then it starts to make a lot more sense. Another example is the dozens of companies working to port Wordpress apps to Shopify. They're not making the apps any better, they're just making them work on shopify by owning their category in the Shopify App Marketplace. Here's one idea I posted on Shopify hoping someone would build it: https://community.shopify.com/c/shopify-apps/how-to-add-a-ta...

All in all, I wish you the best. It seems like your heart is in the right place but you need improvement on strategy. You want to build something that people use but thought experiments aren't the way to figure it out. Coming up with more ideas probably isn't going to work out if you don't understand why the other ones didn't work out. An idea without understanding the context of how it will be sold is only a prayer. Talking to customers is great & reaching out manually is a sales strategy as old as time, but it's hard to build a company out of this without 4+ figure deals.

For me, it was figuring SEO and micro influencers. My first business was CBD products got to ~$500K/month in 2.5 years before selling it. I'm now investing in (and helping build for a few months) a cardboard cat homes business. It's completely unrelated except for the sales channels. It sells exactly the same ways and it hit $10K in its 2nd month of sales. After this 3rd month, it should be profitable and I can step away to help other founders start more ecommerce businesses.