Hi @noobiepie,
If this is ZEC in the transparent pool, first some good news. Your funds are not affected by the upcoming Sprout freeze around Nov 5th.
Transparent ZEC remains spendable after NU7 using modern transaction formats.
I would suggest trying Zkool, the successor to YWallet. It can import older transparent private keys, including the uncompressed WIF format that many older wallets struggle with.
After installing Zkool, create a new account using Restore Account, enter one private key locally, and set a birth height earlier than the original wallet’s first transaction. Let it synchronize before attempting a transfer.