Is it possible for multisig wallets to have trusted addresses? (Dynamic amount of permissions required)
This is not a wallet function. This can be done with m-of-n multisig script.

for example Alice, Bob, Charley, David and Eva want to have 3-of-5 multisig address, but David is manager and it is enough to have 2 signatures for spending if one signer is David. Eva is bigboss and can spend funds alone.

So, the redeem script can be 

OP_3 pubA pubB pubC pubD OP_DUP pubE OP_DUP OP_DUP OP_8 OP_CHECKMULTISIG