So I guess what I really ask is, is there any good documentation that explains how to deployed the newly available P2SH nested addresses? This way we can start moving Bitcoin into the Segwit space and save on cost when we flush a high amount of tx's.
Yes. There is a segwit developer's guide:
https://bitcoincore.org/en/segwit_wallet_dev/ which explains everything that needs to be done to implement all parts of segwit. The BIPs also explain most of this.
Also, as an example to understand the extra space. Say I was the only one that used the newly created P2SH addresses. Would that guarantee my tx included in the next block? Since I could use the extra space? Or would it only be a saving in terms of how big a portion of my transaction would end up in the extra space?
I know its a stupid example as many more would probably end up using the new addresses, but for the sake of understanding, if I am the only one, I assume I get included, right?
I assume the "extra space" you are talking about is the witness data "extra space". That space is for witness data only (and it really isn't actually a separate "reserved for witness data" space in blocks either). Since only the signatures go in the witness data, you still have the rest of the transaction that must compete for the "normal" block space too. There is no guarantee that your transaction will get included in the next block.