I started learning Blender in CG Cookie when they already had hundreds of hours of training with older versions. I also learned all of the creative software I use with the mindset "learn the latest, it's only progressing from there".
The older versions training NEVER felt short. They have a tremendous habit here to teach you concepts, not just what to click. And while it took me a tad longer at a couple of instances because I had to research the differences, it never felt like a hinder. I was learning, I was still using the latest.
I actually even got to halfway the last chapter in this course going through the same. Learn the concept, can't apply on this version? Figure it out... But I just hit a big snag that is actually making me install (and keep until this is past) a second version of Blender. The fill tool does not work as expected, and it lacks some really important features such as the "Boundary Strokes". I'm not a great illustrator and my line work is all open. I'll call that a style, cause I can. But that makes it impossible to do the color flatting process. A big problem, and I tested in on the LTS, 4.3.2, and 4.4.0 release candidate.
I LOVE all the other features of the new version. I like the new brush set up, love the GN integration. But this is big, and I thought I'd let you know, from one "I must use the latest version" person to another. I had to restart a project and am bummed.
I'll be sure to delete this as soon as it's no longer a big deal, but for now I hope it helps someone. I guess the coding difference from Grease Pencil 2.0 and 3.0 will take a tad longer than normal to debug.
Have you tried using radius mode(S after you start the fill) instead of extend and adjusting the length(mouse wheel up/down after you start the fill) until you get a blue line? I've been playing with this instead of using boundary strokes.
***Edit***
You can use page up and page down instead of mouse wheel. I just remembered that you said you don't use a mouse.
Uh, I was hopeful for a sec. But I couldn't get it to work. So you click once to start the fill, then S, then up or down the wheel like we adjust the proportional editing?
The new versions DO have excellent features. I love the consolidation of tools; I love the Gradient tool in edit mode (althought because it works with ANY texture or gradient material, they should really change the name). Even though it is infuriating at times, I do happen to like the assset brush system and it could become potentially better. I hope some of the older tools come back soon (like guides) too.
There's lots of little stuff that still bugs me, and I wish they were easy fixes. Joining two strokes STILL doesn't work - what you get is a new stroke which covers the gap point-to-point, but is not really a join. A custom brush will link in its material with every stroke so you end up with a bajillion materials you don't need. Sometimes copy-paste goes TERRIBLY wrong.
I really REALLY want to start building a new course, but until some of the small glitches that are vital to good work flow are addressed, it will be a course about how to avoid the biggest offenders.
Also - please keep this comment! It is a worthwhile opinion on the state of things currently!
I'll definitely watch the new course when it comes out! But 100% it makes more sense to wait until GP 3.0 is ironed out.
I didn't think I would ever have on-going 2 versions of Blender, but even trying to change my mind and go back (appending my half-started project) to 4.2 didn't work. It was broken beyond repair... The Grease Pencil properties tab on the appended object is fully blank and all layer/points information is gone. At least I can trace over it. Lol.
So here we are. Two versions for now... and I might wait to play with GN with GP later on.
You click once then you can start scrolling wheel it will make blue lines to cover the opening. Once the lines touch fill will work. If you press s to change from extend to radius it will have red circles until you make them large enough to close the gap. At that point it will change to a blue line. I'm still learning how to draw and learning grease pencil. I saw the options on the status bar one day and started playing with that. For me it's easy because I use to have 28 version of Blender. I have it down to 14 now. Although the 2 Blender for artists versions some people don't count.
Ah! I see now! It's probably not working for me because I don't use a mouse with scrolly wheels. I use a drawing tablet / pen 100% of the time. Couldn't get it to work with my usual workarounds (like how I use proportional editing and such).
You can use page up and page down buttons instead of mouse wheel.