Will we ever be able to have totally obfuscated transactions that don't even show up in the blockchain (monero style)?
Monero uses Cryptonote which uses ring signatures to hide the sender of any given transaction such that it isn't possible to accurately connect given outputs with given inputs unless the sender revealed that information. Last I knew transactions, and their amounts, definitely were openly visible on their blockchain.
Somewhat. Amounts are broken up into power-of-10 denominated pieces and each piece may be payment to one or another payee, or change. So the amount is obfuscated by the number of ways the pieces can be allocated into these bins.
So a payment of 100+20+3 could be a payment of 23 and change of 100, a payment of 120 and change of 3, two separate payments of 100 and 3 along with change of 20, etc. When there are more pieces the number of possible combinations increases.
It isn't true, however, that Monero transactions are something that doesn't even show up on a blockchain. They do show up and the total amount (payments plus change plus fee) can be seen as equal to the total inputs, which helps visible integrity of the money supply. You don't have a complete black box like zerocash where certain types of flaws could mean that infinite coins could be created (as was once possible in Bitcoin due to a bug) and never detected. Although you still do need to rely on the integrity of Monero's key images to ensure coins can't be double spent.