middle-eastern questions

I'm familiar with the evolution of the Greek aspirated consonants
(or,
at least, I'm pretty sure I am), but no matter what I read, I can't
seem to get a straight answer on certain pronunciations in the old,
middle-eastern languages. For instance, Anat/Anath or Asherah in
Canaanite. Are the particular sounds I'm thinking of supposed to be
pronounced as a /t/ (or, in Asherah's case, /s/) with aspiration or
as
a voiceless fricative? I've always assumed the former, but when I've
read through certain materials, say, in Akkadian, I see things such
as
an s with a hacek. E.g., Ishtar (which I formerly thought to be
/'ish·tar/) spelled as Is^tar (which would seemingly indicate it
should be pn. /'if·tar/, the f being the esh fricative I don't
know
how to write out in normal text.) Can anyone help me out with this?
It's one of those things that's been annoying me for years.

Something else I don't understand is the whole
Canaanite/Phoenician/Hebrew distinction. At some point in the past,
I
remember reading that Hebrew was the recently-resurrected Canaanite
language. Sounds strange, but renaming it so it wouldn't be confused
with the older sounds logical enough to me. However, occasionally I
run across a word or whatever that should be, in that case, described
as "Canaanite" but is described as "Hebrew", and vice versa. Is this
just fairytale? It almost seems like it to me. Similarly, I had
always thought Canaanite and Phoenician were one in the same. What
is
the distinction between these three?! Distance in provinces or
something of the sort? Some type of political division? Mere time?
I'd love to understand this once and for all.

Again, TiA. I appreciate it.

- Eris