Honestly? Many things:
-It's tricky for a non-technical user to setup
-It disrupts their regular workflow
-People get frustrated with speeds of Tor etc
-People get frustrated with Captcha (Dam Cloudflare!) and other things caused by using Tor in a safe manner.
-People get annoyed as it doesn't solve their problems and exposure on mobile
-You have to restart to run it
-They can't run their regular programs on it - MS Office, Outlook, Adobe, etc.
-It's Linux based, so a big mental jump for most people coming from Windows (or most people not at the command line on OS X)
-It's hard to access files on other drives
-Documentation and TAILS is only available in certain languages
-It often has driver problems - e.g Macbook Pro 2015 WIFI issues
-In developing states, computer literacy is low, so anything other than the norm (Windows) is confusing
-In developing states, hardware tends to be slow (often counterfeit) so running TAILS in RAM is slow
-People lose the USB sticks they put TAILS on (also many counterfeits, so they often fail or have a false size)
-TAILS often requires training, which not everyone has access to
-Skills fade for digital security training with journalists/activists is often quite high, especially if they don't need it that often.
-the list goes on............
Don't get me wrong, I think it's great (as is Qubes, Subgraph etc) but we need to be realistic about it's limitations for the majority of people. Especially if we want to be sensible and try to tailor advice, training and tools to their realistic threat models.
P.S Definitely, I'm on the West Coast probably once a year. Ditto you if your ever in Dublin (Ireland, not that fake one in California :) or London!