This post is really two separate groups questions, but I'm putting them in the same post for the sake of having everything in one place. I apologize for how verbose this is. To make reading it easier, I've put the meat of each section in bold, i.e. the actual questions I'm seeking answers for; the rest is background info explaining my specific needs. Putting it under a cut since it's so long. This post is also on my Tumblr.
Edit: I use Windows and have an iPhone, if that helps with specific software recommendations, though both of those might change in the future.