I worked for a very small online retail company recently (I know it's not exactly the same but in the same vein) and raising the price for $18—$40 items by $5 had zero affect on the number of people placing (sales weren't amazing but not bad).
But ya, in the first line you say you made $15k over....... FOUR YEARS? Obviously that's a bunch for some people, but certainly not MOST people in tech?? You could have made much more and had a lot more fun bartending or even being a barista.
Having read the whole post... keep it up! Just raise your prices by... like, a LOT! Like, a lot a lot!
I don't know the original attribution but it's something along the lines of "don't be afraid to fire unprofitable customers." If you have a customer who is drowning you in support tickets, and just not "getting it," politely tell them "sorry it's not working out" give them a refund and cut them off.