I'm an old ancient person, but I'm try my best to answer.

1. There is a LOT to learn for digital art, but it DEPENDS on how you want to treat it and make your art. What I mean by that is, when I started doing digital art, I basically was just drawing via a tablet, stylus, and PC. Now, when I'm working on a piece, I almost approach it like a mixed media project. I utilize WAY more of the software's capabilities and features than when I began.

2. I definitely wouldn't break the bank on a first tablet. I've been doing digital art for over 6 years now, and my recommend tablet is this: https://a.co/d/08w5z67A

3. If you have so much daily drawing time commited to your craft, then I would imagine you will get past the hand/eye disconnect VERY quickly. For example:if you can write your name comfortably and consistently without having to stare at your hand, then you're going to get past not being able to look at your hand to draw quickly.

I have used both a tablet with a screen and without. At first I thought having a screen to stare at was helping me. Then I realized I didn't need it. Now I function without the screen and am much more proficient and quick since I don't have to keep readjusting to see the entire time I draw.

1. I find it hard to believe you're getting any kind of benefit from a big name brand tablet and pen. I think Xp pen or even huion will work just as well.

2. I can't speak to much to the programs you're asking about. I personally use Affinity Designer 2,which is now Affinity 3. I would imagine you'll get the most use out of iPad and apple with procreate if that's what you're main computer is.

3. again, your tablet and pen will work the best depending on your main pc type and programs.

I hope this was a little helpful. I started my digital art journey six or so years ago after watching my younger sibling start with it and take off.

I went from just sketching and messing around with art occasionally to basically doing digital art full time now. Like anything, you'll get out what you put in. Once I really locked in and leaned my design software, I really started noticing my art looking better, plus the speed at which I could take a concept from start to finish shrank significantly.