I know that when I learned to program in Perl, the course seemed much smoother than when I set out to learn other languages later. But then I realized that there were several factors:
  1. I misremember how long I took to learn Perl. It feels like I picked up the book and was writing it fluently a few weeks later. But I know that there were important parts of the language that I learned a lot later.

  2. When I was a baby in Perl, I tried to do baby-like things with it and succeeded. Now when I look at new languages, I over-reach. I immediately try to do things that I know how to do in Perl, and don't know enough to do them.

  3. When I learned Perl there was a constant feeling of accomplishment because I didn't know any way to easily do what I just learned. In other languages that sense is gone because whatever I just learned, I already knew how to do.

As for context, I think that it is important to know about context, but ideally it sinks into being a reflex. It's handled by the same part of your brain that handles grammar and knows when, for instance, you have to switch from past to present to future tense. Certainly I am not conciously aware of thinking about context, though I can tell you what is going on with it at any given moment.

Cheers,
Ben