I tried to 'send to myself' in the official client. And that tx will never confirm (That was in 02/2013 ... still not confirmed) So I just assumed that transactions from the same wallet into the same wallet wont confirm.
The tx did eventually confirm. So it turns out it was valid ... which kind of makes me wonder why my previous attempt to send to myself was invalid. My whole purpose for using MultiBit in the first place is to have a completely separate wallet to consolidate my coins lacking the ability to do so in Official client.
The MultiBit tx
http://blockchain.info/tx-index/9375925ed95d85cd9b5ecda6332c814c35ebf04124ac625da4c0bf10ab597767And the Official Client tx, which seems to have never hit the blockchain, yet is stuck unconfirmed in my client
Status: 0/unconfirmed
Date: 27/02/2013 22:07
From: unknown
To: 1DNNERMT5MMusfYnCBfcKCBjBKZWBC5Lg2 (own address, label: BitHits.info)
Credit: 0.0002388 BTC
Net amount: +0.0002388 BTC
Transaction ID: ee082cd20d6bd35380d1311f84ca4ff967d72821aa12ca3f354718c3a5208e66