Fantastic thread @Makoto Nakamura - I'm new to the forums but am familiar with the Scottish non-league journey having managed Orkney over the past 3 FMs, and not once got out the North Caley League! I know just how frustrating this league can be. I will be giving it another go this year, but I think you've got it in you to crack this league (and the horrible playoffs that come along with it). If I could lend a piece of advice it would be to perhaps abandon prioritising the cups (you may be doing so already) apart from the Scottish Cup obviously! From my experience post Christmas the fixture list does dry up a little and as it becomes such a short league season, the emphasis and pressure on each league game heightens, so if I had spare weeks I would stick a friendly in just to keep up the sharpness.
Really enjoying the amateur starting point you and others have done this year, despite restricting yourself to Highland only players you've done well hoovering up talent from higher tiers, putting you a class above pretty much everyone. I don't think this will be your ceiling, as long as you can stay consistent, keep up momentum and morale, and stay lucky (we all need a bit of luck), you'll get there in the end. I will definitely be loading in the amateur leagues for my save to keep an eye on all the teams you and the others have discussed above - might even find some players to pinch!
Will be following along the journey.