Well, you’re conflating money and time. Please stop doing that. It’s a tradeoff. In some cases, it’s worth paying. In others, it’s not. You seem to feel that money is the better option for you, and that’s fine.
As for “payment” in time, that can always be reduced. Also, someone who only handles this kind of thing once a year is likely going to spend significant time looking up how to do it every time. For professionals, we have the steps memorized. Some traditional providers also offer an API for certificate issuance that can be automated (it’s how CloudFlare does it).
Regardless, there’s also the value argument. You have the knowledge and money to work the traditional way. The majority of people with their traditional blog or small-business site won’t have the knowledge. Offering an automated no-cost solution is a huge value to those folks. With a short time period, it basically requires that hosting companies (or the hosting software they use) integrate the process to make it entirely automated and avoids the knowledge issue.
For my use case at work, I can automate everything away except the initial setup, which would cost the same time regardless of the option. As a bonus, I don’t have to spend four hours every year with each customer walking them through the certificate purchase process because they aren’t technical.
StartSSL is free for non-commercial use ONLY. If you want to use their certificates for business, you have to pay. It’s actually in their terms (and they will terminate accounts if they find you using a free cert for your business). WoSign looks interesting, I guess. I may have to try their process at some point.
I hope they finally do get trusted. It’s been over a decade now, and it would be nice to have several options. As it is now, they have no major acceptance and no cross-sign with a root that does.