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2

I would not consider your case to be a cascading encryption. The reason why is the fact you need multiple interventions before getting access to your file. Here is what I would consider a cascading encryption (let's go crazy) : $$E(k_1,k_2,k_3,m) = \text{KEYAK}(k_1,\text{NORX}(k_2,\text{AES}(k_3,m)))$$ which you would decipher with : ...

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Note: I won't recommend a specific library for these, because this would be off-topic and the risk would be there that this gets outdated sooner than later (especially as soon as CAESAR finishes). This is a very standard solution to the authentication problem although usually one does do both (e.g. passphrase and keyfile). On the conceptual level any ...

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Would this or any other information about the data help with decryption? What you are looking for is called a known-plaintext attack. Nowadays secure encryption algorithms are expected to be secure even against chosen-plaintext attacks (a strictly stronger assumption), like DiG mentions in the other answer. If knowing plaintext data would help decrypt ...

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I recommend you will read a bit about chosen-plaintext attack. If the scheme you are using is CPA-Secure then even when an adversary is choosing two different plaintexts, giving them to the challenger and then the challenger picks one of them, encrypts it and sends it back to the adversary - the adversary won't have an efficient algorithm to find out which ...

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Since it uses 128-bit encryption, there are at most $2^{128}$ keys. So if the password is complex enough, you will need on average $2^{127}$ tries. Which is about $1.28×10³⁴$ seconds, or so long that yon can't live that long.

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I had only a quick read through the source, and I am not particularly fluent in C#, so I may have gotten something wrong. That said the process appears to be: Generate a random encryption key, encrypt the database with it. Generate (up to six) HOTP tokens, derive a key from those, use that to encrypt the database key. To read: Ask for the HOTP tokens, ...

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