I have only one currently, I can't grasp the idea of having hundreds of addresses.. Since I use blockchain. Can anyone clarify why you need 100s, and is it better to use an actual program then a site like blockchain?
Sounds worthy. But, how do you change the default behavior of the blockchain.info wallet, and how do you manage key backup if each transaction creates a new set of keys?
blockchain.info is very difficult to use in a privacy protecting way because you have to change
your behavior. You have to tell it to create a new address each time you want someone to sent you BTC (not too bad). You can use the shared send advanced function (costs a bit more BUT it will automatically generate a new change address for every send and you will be mixing your transaction in with a lot of other transactions and this is
great for privacy). You can generate your own change addressed by hand and set up your transactions to have good privacy behavior in the advanced send tab but you have to do this all by hand. I really love the blockchain.info wallet and I use it whenever I want to to a coinjoin (shared send) transaction but you have to be very careful how you use it.
Then, here it the real problem with that wallet: you have to remember to back up the wallet pretty much after every transaction. I have mine set to send me an email containing my encrypted wallet after every new keypair is created. Painful. And because I am using the email system it is not that secure, so I only use it to hold a minimum amount of BTC.
That is why I highly recommend
deterministic wallets. Get yourself a deterministic wallet and you will never look back. All you have to do is keep the seed safe and secure and then you never have to make another backup again(!) because every receive address and every change address is determined and can be recovered from that single seed. Very cool.
So, you back up the seed on paper, make a few copies, laminate them, keep one in a safe hidden location in your house, another in an offsite safe location, etc. You can even be very clever and store half the seed one place and the other half at a different location.
Of the deterministic wallets the Trezor hardware wallet is probably the safest but it costs $120 for the device. My favorite Android deterministic wallet is "Wallet32". There are others to choose from just look around for them or I will get a list together and post it if I get time.