To add to @Robusto's answer - regarding the origin - the following seems more definitive and is taken from "The Facts on File dictionary of clichés"
To be extremely tired or about to
collapse; near the end. Despite the
implication, this term never meant
that legs were in any way serial—that
is, beginning with the first and
ending with the last. Rather, it uses
last meaning “near the end” (of one’s
energy or life). The expression was
already used in the sixteenth century;
it appears in the play The Old Law
(1599) by Thomas Middleton and Philip
Massinger: “My husband goes upon his
last hour now—on his last legs, I am
sure.” In John Ray’s Proverbs (1678)
the term is defined as meaning
“bankrupt,” and since then it has been
transferred to anything nearing its
end or about to fail, as in, “This
cliché may be on its last legs.”
However this link dates "The Old Law" as
On his last legs. The Old Law
(1618-19), Act v. Sc. 1.
The exact text as it appears online
EUGENIA My husband goes upon his last
hour now.
FIRST COURTIER On his last legs, I'm
sure.
EUGENIA September the seventeenth, I
will not bate an hour on it; and
tomorrow His latest hour's expired.
The OED's first citation for "bullet point" (in an online draft addition) is in 1983:
1983 Datamation Sept. 221/1 Each chapter concludes with a bullet-point list of ‘things to think about’ or ‘things to remember’, which is particularly helpful if it's been a few days between chapters.
The term "bullet point" originally seems to have meant not the typographical symbol, but the text marked by the bullet symbol • in a list. That is, a bullet-point list is a list of points you are making in a presentation. For example, a Harvard Graphics manual (the predecessor of PowerPoint) in 1990 says:
Pressing Enter a third time creates the first bullet point and places the cursor to the right of the bullet.
However, the term "bullet point" was very quickly transferred to mean the symbol as well.
I have a theory of when and why bullet points were introduced, but absolutely no confirmation.
Looking through 19th century books, I can't find any bulleted lists. Lists are either indexed by numbers, or items are identified with spacing and indentation. When typewriters started being widely used in the early part of the 20th century, people started preparing typed documents with less care than they had taken with printed materials, and it was too much trouble to renumber lists while editing documents. So they started using asterisks instead of numbers. Printers took these lists marked by asterisks and used typographical bullet symbols instead.
Best Answer
The phrase is a slight variant of "Is this the hill you want to die on?" which is often used in the military when discussing holding a position at all hazards. In this case, the answer is assumed to be "no".
When you decide to defend the spot to the limit, then "No better place to die" is often used. I have heard this used for many actions, back to the US Civil War and it probably was old during Ancient times.