The original theory was that the Constitution did not so much guarantee rights as serve to limit the power and scope of government. The Bill or Rights was not meant to be exhaustive, just hit the high points. That idea got lost somewhere along the way
The core issue of the second amendment is whether it is a collective or individual right. Saw an analysis by a grammarian that argues that, given its structure, it is clearly two parts; validating the right of states to have a militia and making possession of a weapon an individual right. Can that "right" be regulated (say by requiring registration or limiting the nature and type of weapons available? Such is what courts are for.
The interesting one to me is the 14th as just what constitutes "privileges" "immunities" or "property" (which under law can mean far more than real property. Apparently some of the libertarian civil rights activists are supporting cases that seek to test the limits.
"The language when each amendment was written reflects the times it was written, but does that matter? Or should it? The intent of the amendment can only be seen in history but do we interpret it in those times or these? Or does it matter?"
If you read the Federalist papers, I'd say interpretation was expected. The problem seems to be when the interpretation gets really creative and just how deeply someone reads into an Article or Amendment, either textually, structurally or sometimes by relying on ouija board.
Personally, I favor the idea that unless specifically limited by state law, the right exists.