For your first question, I think the answer depends on what sort of art style you're aiming for. If you want to show linework, or have an outline around your character, your canvas will need to be a certain size, depending on how thick your lines are. Some of the games that tout their hand-drawn art have very high-resolution sprites that are scaled down at run-time to match the player's resolution settings. In my view, hand-drawn art is just going to look like pixel art if you're drawing at a very small resolution. Also, if you draw something at a very high resolution, and scale it down to a very tiny resolution, there's a good chance some details will be lost, and you'll have to do a second pass at the pixel art-level anyway. So, if you're going the hand-drawn route, I'd say to work with a larger canvas.
I'm afraid I don't have much to offer for your second question, but if I were hand-drawing tiles in Photoshop, I would either set up a grid of the tile size that I'm aiming for, or use guide lines.
Hope that helps!
Gotcha! That certainly helps. I think considering my art do feature thick outlines and the designs for my game are, for the most part, very minimalistic, there is little reason not to work with a larger canvas and then resize it accordingly later. Though I believe I should come up with a few templates to make sure everything is consistent. Say, if there are two characters the same size, but I draw one in a 4K canvas and the other in a 1080p one, when resizing them, I believe stuff like the thickness of the outlines will look different between both sprites, right?
Since my project takes a lot from the old Game Boy Pokémon and Zelda games, I can start by multiplying the dimensions of the sprites in those games and using them as templates.
Thank you!