Unless you made a mistake somewhere, and the random isn't as random as you think.
If you have the technical knowledge, feel free to check it here:
https://bitcointalk.org/index.php?topic=5432897.0"Vampobit" was my original account here, but for personal reasons, I don't want to be "vampobit" anymore. I may still have access to it though.
As far as randomness is concerned, I have decided to follow a very simple approach. I roll a dice 256 times and if it's 4-6 I sign it as 1, else I sign it as 0. Then I have my entropy like 100010101....
Of course

Having a dedicated system for offline signing is easier than getting one each time you need it. And if you have said system already, it's easy to import a paper wallet when you need it.
I like to use a wide variety of wallets, depending on my needs at the moment.
Sure! I have a 2-of-3 multisig and a singlesig with passphrase personally. But I totally agree with you.