Creating a 7 of 7 multi-sig private key should be less risky than creating a private key that requires one signature to spend coin (assuming you can easily replicate the procedure to keep each private key secure).
I mean, sure, but that is completely irrelevant to what we are discussing here. Paper wallets which are generated via flipping a coin and paper wallets which are generated via third party code/software will be exactly as easy or difficult to spend from as each other, and exactly as secure or not to spend from as each other, depending on how and where you opt to import the seed/private key. Generating entropy by hand decreases your risk from malicious or flawed code generating non-random entropy. It is irrelevant to the spending process.
This is not entirely true, see
this thread. In addition to leaking your private key, it could leak additional information.
Perhaps I didn't explain myself clearly. My point wasn't "There is no method by which it could leak information", but rather "There is no method by which it could leak information that I can't detect before I choose to broadcast my transaction". If the wallet attempts to reuse a k value, as in your example, then I could detect that by reviewing the source code and realizing it is not using a deterministic process for generating the k value, or by generating multiple different transactions and comparing the R values. The amount of trust you need to place in an airgapped wallet is much lower than the trust you place in any "live" software or mobile wallet, which could steal all your coins immediately upon you importing your seed phrase.