I am looking, specifically, for a step by step example transaction of sending Bitcoin which uses an actual transaction (How To Redeem A Basic Txn, from a few years back, does a great job of outlining most steps of sending a raw txn but does not use a real TxID).

I have played around with both the Python pybitcointools library, the SX library and JSON output from the Bitcoin Core client (Bitcoin-QT, Bitcoin-cli, Bitcoin daemon) but have yet to find an actual step by step guide using raw transaction output (single input / single output Bitcoin txn, ie not multisig).

Hopefully the bounty will bring a step by step example transaction (with private keys for the sending address) will bring an answer showing how it's done and, specifically:

how the ScriptPubKey element fits into the raw txn

how the ScriptSig element fits into the raw txn

how the txn is signed (with DER encoding).

EDIT: I think the best resource is Ken Shirriff's Bitcoins the hard way: Using the raw Bitcoin protocol, but again, there's no single source online that answers my question without skimming past areas like scriptPubKey, signing etc.

When I activate the bounty, if you can answer this refer to this Tx as it can serve as the actual example (ie I'll provide ~$1 in BTC and private keys for 1From/1MBngSqZbMydscpzSoehjP8kznMaHAzh9y if interested)

EDIT 2: The RoyalFork Blog: Deconstructing Txns provides an unbelievably good reference for interactive Txn creation