What I want to know is can I send funds FROM my segwit bc1 address TO both legacy and wrapped segwit addresses without issue? I don't want to try and send funds from my bc1 address to an address that starts with a 3, only to have it get lost in the ether.
Yes, there's no issue with that at all. Electrum supports all the above formats, so you can easily send bitcoins from your native Segwit wallet to legacy and P2SH wallets, and vice versa.
Secondly, is it possible to transfer funds between my two wallets, which are on the same computer, locally... without sending and having to pay fees?
You can't import private keys using a wallet that has a seed. You can sweep them, but that obviously incurs fees.
In the current version of Electrum, it appears the only options are to create a wallet from seed or use imported keys. If you create a wallet from imported keys, you won't be generating new keys for use.
The best option is probably just to use the two wallets separately and when needed, send/sweep coins between them.