@cypherdoc Sorry about the confusion, I was tired and not really in a good place for a coherent response.
Whether the transaction shows up in the GUI is up to the implementation, however I will answer this in the context of Bitcoin Core.
When a non-segwit wallet receives a transaction with a segwit output, it does not recognize that the segwit output belongs to it. To old nodes, the segwit output is a nonstandard output because it is of the form
This will not be recognized as belonging to the wallet even if the <20 byte hash> is a hash160 that belongs to the wallet.
Non-segwit wallets will only recognize p2pkh, p2sh, p2pk, and raw multisig as outputs that belong to it.
To send Bitcoin to non-segwit wallets is really part of the implementation of segwit. Since p2pkh outputs are universally recognized as a normal address and p2sh outputs as a multisig address, segwit will not be trying to change that. If you are sending to an address, then it should always be sent as a p2pkh and p2sh output regardless. When you enter a normal Bitcoin address, the wallet should (and will in the case of Bitcoin Core) always create a p2pkh output and never a segwit output. With p2sh addresses, it will always create a p2sh output because it isn't possible to know the 32 byte hash required for a segwit script hash output.
There isn't any incentive for the sender to be creating segwit outputs anyways. There is actually a negative incentive for doing so because the receiver may not have a segwit enabled wallet. It can cause disputes and it's a total dick move. No wallet developer should write their wallet to create segwit outputs by default, only be able to handle them if people do decide to create those outputs by hand.
The part that makes sending between segwit wallets and non-segwit wallets is the use of segwit outputs nested inside of a p2sh address. Because it is p2sh, the sender sends it using the standard p2sh format but the receiver can still take advantage of segwit's benefits. And spending from a segwit output to a non-segwit output is fine too because inputs and outputs in a transaction are not linked together.