(1) Find someone you can pester with questions. (2) Understand the basic workflow. (3) Start by copying and modifying existing designs. (4) Build solutions using functional modules, and version these. (5) Bench test everything. (6) Be aware of startup and edge conditions when designing. (7) Take notes on all design changes or prospective changes, hypotheses and findings. This process will greatly accelerate your learning. This is easier if you have LXI-capable equipment and can capture test information easily. https://github.com/lxi-tools/lxi-tools
I'm also a hobbyist. It's daunting, but there are a lot of good videos on Youtube.
I think the most frustrating thing is just trying to find the correct symbol and footprint for the part you want. Sometimes they're hard to find because you have to understand Kicad's organization scheme. Sometimes what you want isn't there at all so you have to make your own symbol or footprint or both. (Which, to be fair, is reasonably easy to do.)
Exporting a Kicad project's gerbers and drill files to JLPCB is surprisingly easy, but to use their pick and place service is more work. (I just ordered an assembled board for the first time, and had to manually reposition all the parts in their web interface because the position file put all the parts offset way off to one side and with the wrong rotation. Not sure if I did something wrong or there's just a bug.)
I think Kicad just takes a long time to learn. There are a lot of very powerful features that you might not know about at first. Kicad also expects you to do things in a particular way, and if you don't it tends to cause problems.
