I can identify with most of what you are talking about here. I also struggle with the same thoughts and never sure what is the best way to take really is. So, of course the most ideal think would be to have a art dealer who would do all the selling, promoting, etc...but, somehow I realise my style is not something galerists can be sure to sell, I don´t play up enough of the crazy artist (because these paintings would only commercialise this way) or I´m not modern/coolenough (in a "latest trend" way)...so, because I want to be free to do the art I feel from inside, I don´t count on selling it to survive. If I did that, it would affect the way I paint. I´d be painting to be liked by others. I chose to have a regular income from another source and keep the discipline of painting to be free. I am just sharing my perspective on this. You might find some info interesting or not. Who knows. When I have to price them I´m always in doubt, but I do use my emotional connection to them to have them priced, the more they mean to me and I still need them around the higher the price. When I´m done with them, even looking at them I can let them go very cheaply or give them away. Paintings have lessons to teach me, usually, so they tell me. i ask them.