Different Wallets and ScriptSig does it help obfuscation? my question is this if you have coins that you are looking to break an identity link (not using mixing services)

does using multiple wallets if you send different amounts of bitcoin help obfuscate the funds etc

so I have three HD Wallets
i have 5 btc send 1.33 BTC to each wallet

when the funds are spent they all use different scriptsigs to unlock the funds right?

so on the blockchain it will show different scripts spent the inputs.

Does this do anything?

Last question, do HD Wallets use a new script sig for each transaciton since they are using a new Pub and Priv Key for the transaction.

Am I Missing anything?
The way transactions are associated with one another has to with the transaction's inputs.  When you send bitcoin, you are usually using multiple inputs, each with an address you control.  Anyone looking at the blockchain now knows that the same person controls all those addresses.  Now they can cross reference those addresses with addresses identified as "change" addresses from other transactions, and can be reasonably sure that the inputs to those transactions are also controlled by the same person.  This process can be repeated, which gives is a reasonable guess at which addresses are controlled by a single entity.

A wallet can only combine inputs that it controls, so using three wallets will show up as three controlling entities with blockchain analysis.  However, it will also reveal a lot of cross payments between these wallets, leading someone to assume they are somehow connected, possibly being controlled by the same person.

As for your other questions, as long as the addresses change for each transaction, so will the scriptPubKey and therefore the scrpitSig of the spending transactions.

Just remember, it's not the similarity of the scripts that allow blockchain analysis, but the association of the inputs and outputs.