JackJack mentions that pywallet didn't recover compressed keys. Could that be why i'm not able to recover anything from this wallet? Does the old pywallet have trouble recovering and dumping newer wallets. Does a wallet from 2015 fall into this category? Cheers.
Not sure about "recovering"... but it certainly dumps "compressed" keys... the thing you have to remember, is that the private key itself is not "compressed" or "uncompressed"...
It is the
public key (and the subsequent hash160 "address") that is "compressed" or "uncompressed". The private key is always a 256bit number.
I think the "new" fields were added when HD wallet support was introduced which was in v0.13... which was released in August 2016... so a wallet created in 2015 should be the old "non HD" wallet type. However, if it was subsequently opened in a newer version of Bitcoin Core, the wallet file was likely "upgraded" (not to HD, but to the new format) which may have added in the fields that cause issues with PyWallet.
This is why I recommend making copies of the original 2015 wallet.dat file and working on the copies.
Again, have you simply tried opening one of the copies of the wallet.dat in Bitcoin Core and using either
dumpwallet or
dumpprivekey from inside Bitcoin Core? It would be much much easier than trying to deal with PyWallet and it won't matter if the wallet file is old version or new version.