I've been using git annex for the last few months and there are a lot of things I really like about it, but I continue to run into frustration after frustration and it is really hampering my experience with it. I'm not sure if the frustration is coming from my ignorance, inexperience, the fact I'm using it on a windows machine, or whether I have unrealistic expectations for it. Let me explain how I'm currently using it, and maybe people have suggestions on how I can make my experience more fluid.

Currently I have a several annex repos on my laptop and copies on two separate hard drives. Over the course of a week I'll add and refer to stuff in the annex repos on my laptop, and then once per week I'll sync the repos with my external hard drives and remove content from my laptop to free up space. Eventually, I'd like to write a script to handle the syncing process.

I continue to have issues. A few weeks ago I accidentally added large files straight into git and not knowing or understanding the documentation enough to remove them I eventually just removed and recloned the repo. To this week, being unable to sync my repos due to filenames that are too long. I know neither of these examples are really issues with annex itself, but they are issues which have come up while using annex which gives me bad mental associations with it.

I guess this is more venting frustration and looking for guidance rather than a specific question. I've read through much of the documentation, but do I need an understanding of the internals of git and git annex so when something goes wrong I know how to fix it? Where is a good place to start learning these? There have now been a couple issues around being on a windows machine, is it even worth using git annex on a windows machine? Do people have any tips on how I'm using git annex which may make my experience better, like a different workflow or something?

(I'm still having the filenames issue, which from what I can tell the only real solution is changing the name. If anyone knows a better solution it would be appreciated)