Couple of questions for ya:
1) Do you use TAILS at all in conjunction with a monero wallet? I've read up on how to install it onto TAILS but seems rather annoying to always have to install it every time you boot up TAILS
2) If you don't use TAILS, what's your course of action? I'm just confused as to how you would get it onto the market I guess since monero wallet isn't integrated into TAILS like electrum is.
3) Shapeshift... Good or bad? Seems to be the easiest way to convert any coins to monero, but been hearing how it's untrusted.
You must be running tails 2.12 or higher to run the monero gui. I would not download the entire blockchain with tails, but instead point it at an onion node.