Good point, Ashlea. Chonologically speaking, you should read
'The Silmarillion' first, but, as you said, in order to make things a whole lot easier on yourself, start with
'The Hobbit', then
'The Lord of the Rings', and
then 'The Silmarillion'.
Mind you, the latter is nothing like the former two. While
'The Hobbit', and
'The Lord of the Rings' read like an adventure-story,
'The Silmarillion' reads more like a history book. It's names and dates where ever you look. I didn't enjoy it that much, actually. It was a bit of a letdown after the highly enjoyable
'The Hobbit', and the massive
'The Lord of the Rings'.
So when you look at it from
that point of view, you
could start with
'The Silmarillion'. That way you start with the least enjoyable one (in my humble opinion, of course), and you end with a bang.
as for other books on the Ring, Hobbits, Elves (or Elfs, whichever you prefer) and Middle-Earth, I can't help you with that, simply because I haven't read any other ones than the aforementioned three.
Cheers, Martin