I had to maintain a lot of old custom appliances and the like for which no ready replacement existed. Niche stuff where you had one or two vendors in the whole arena. If they were running on Apache, it was hidden somewhere with a big "WARRANTY NULL AND VOID" sticker. For all of these custom jobs, HTTPS was an afterthought, if it was present at all. For these, I had to generate cert requests through a menu system, load up certs through a menu system, and the like. I couldn't just CertBot it. That's never going to happen.
Frankly, the latest cult fad ("all must be encrypted, heretic!") has not made my life easier nor brought any benefit to my users. Nobody was going to MitM for this stuff. It's just another tiresome fashion like the people who relentlessly put W3C validation boxes at the bottom of their webpages, only now it is getting shoved through by the same browser vendors who wonder if us mere mortals need to see URLs at all.