I don't block out or do any underpainting. I just sketch and then start painting just because I already know how the painting is supposed to look like and where the color is supposed to go.
I do want to print my paintings. I want to create something called a MoonBox and inside have several products that have my artwork branded on to them. So a MoonBox of my first painting, End of the Rainbow. I would put in the box an art print, a poster, a sticker sheet, a pot of gold enamel pin, a bookmarker, etc. Those all require specific canvas sizes to be done at and if I'm painting really small its not going to look good when its printed.
If I went vector I wouldn't have to worry about canvas size and resolution at all. At all, at all and it would make my life so much easier instead of overthinking all this. I've been eyeing those illustrator brushes for THEEE longest time. I love Von Glitschka. I just never bought them because I don't have money to spare right now, and this product isn't for cs5 so I can't use them. I did, however, purchase other "painterly" brushes by the artifex. They're ok I just always raged quit adobe illustrator just cuz its hard to get the same style using his vector brushes. Its so much easier to paint in photoshop than in illustrator because I'm able to blend pixel easily and get the effect and colors I want.
I used to be an oil painter, and now I'm going digital. I'm channeling everything I know about oil painting into digital art and its pretty easy to make good art digitally. At least, for me. Those vector brushes by Von are exactly the same style as my style. My style is just painterly brush strokes, outlines, and small paint spatters. I think they'd be very fitting for me.
I think I should work small, sketch out my painting, paint, finish that painting, and then bring it into adobe illustrator and then vectorize it using von glitschkas brushes. That way I finish paintings fast, use those paintings as my finished paintings for my 1,000 paintings, and then create a vectorized version of those paintings in illustrator for print later. That I can put out paintings fast but create a vectorized version of those painting for print later becuase I really want to brand my art on to products. I want to take those 1,000 paintings and brand them onto shower curtains, bed duvets, posters, billboards, phone cases, t-shirts, etc. I need to go vector so I think I should have 2 styles. A photoshop style and an illustrator style. BUT paint small in photoshop so I can put out paintings fast.
Also, I really like that goal you suggested because I hate starting a new painting, start the sketching, and then cringe when I have to start coloring the painting. I feel like I shouldn't start any new paintings at all. I should sketch first and knock out several sketches for all the painting ideas I have in mind. Set them aside and then move on to coloring one painting at a time. That way I'm doing more sketching than painting and getting all my ideas out. I think that'd be a great series for my youtube channel where I showcase the sketching process of all the painting ideas I have.