I thought it might be worth giving a little update. Ive been playing with KiCad (6.0.5) on and off over the past month or so, and long story short, it hasnt been a painless experience, but not as painful as I might have thought it would be to switch to another PCB CAD package. There have been some frustrating times, and a bug that Ive had to work with in the symbol editor (hopefully that is fixed in 6.0.6), but generally I would say the experience is positive.
I think Ive pretty much mastered making my own footprints and symbols, and have managed to put together one simple board and sent it off for manufacturing - it came back exactly as I would have expected, so thats a good sign that I might have figured things out.
I have a more complex project in the works, but theres still a lot of work to do on that one before I go ordering PCBs including building a prototype first. And I have a second project that I am currently prototyping/breadboarding that I'll get to some time in the next couple of months.
In summary, while I think EAGLE does some things better (or in a way that I prefer), there are also aspects of KiCad that I like, and I think it would be fair to say that I wont be looking back. If youre stuck on what to do post EAGLE, my advice is jump into KiCad sooner rather than later.