The biggest "obstacle" for a first-timer with Linux
(I've been 'in the business' for twenty-five years and I felt it too!! ) is that it is
so different from what you are probably used to.
Companies like Microsoft and Apple are very, very good at presenting what is actually an
insanely-complicated technology ... an operating system ... in a way that, say, "your grandmother" can actually
ignore. In other words, they have become pretty darned good at presenting it as "a consumer-electronics never-mind the little man behind the curtain
thingy" that the user will happily take for granted.
When you dive into the Linux world, you will find that you actually have to
learn about quite a number of things. You will find that, in places where you never dreamed that 'a choice'
existed, you are actually presented with 'a choice' that you have to
make! You will find that "there is more than one way to do it." You will
also find that you are leaving-behind your compatriots who have utterly no idea what you are talking about these days.
(And in time, you will regard them with 'a curiously condescending smile...')
When you dive into the Linux world,
don't re-configure your existing "war horse" computer... grab that 'old' machine out of your closet instead. Dust the 'old' machine off, plug it in
next to your "war horse," wipe its hard drives clean, and dive in.
"With such a machine... what's the worst that could happen? You'd have to start over again from scratch... 'so what?' You did that anyway!" Prepare yourself: this is a learning experience, and one of the things that you will have to learn is
what you have to learn! This is a learning experience that will make you feel like an absolute idiot.
But... it will also open up to you an entire
world of computing that you never knew existed,
and that you will wonder how you ever did without.
You can expect the learning experience to take you
at least a calendar year for "basic skills," and a full two to three years for serious proficiency.
But never mind that! Dive in!