Ah. For security 3, instead of having to transfer the shares to you and getting security 1 & 2 some time later, you could set up a simple automated site that dispenses Sec1 and 2.
Use the transfer_asset API call in btct.co, or perform HTTP POSTs (login, transfers) for BitFunder.
You don't want to spend your time dealing with requests that could be automated, and it should take around 20 minutes to cook this up anyways. No account system needed, just enter your username and you get an address to deposit to. For security reasons, you don't even need to give the site access to the private key, it just needs to query the blockchain to see if the appropriate amount has being received or not.
Well if it takes off I'd do it via a bot anyway. Bot would just look for transfers in on my account then do the correct transfers out (been meaning to write this for a while as part of my long-delayed trading bot update from the old GLBSE one I wrote).
Problem with doing initial sales off-site are two-fold:
1. Extra risk for investors (that my code is buggy, that my wallet gets hacked etc)
2. Reduced transparency (can't immediately verify total balance in one place) and ability to be audited.