If Alice gives Bob 1MsHWS1BnwMc3tLE8G35UXsS58fKipzB7a, is there any way Bob can safely issue Native P2WPKH outputs to Alice?
No, and the whole issue of compressed vs uncompressed is a red herring. If Alice gives Bob 1MsHWS1BnwMc3tLE8G35UXsS58fKipzB7a, she is saying to Bob “I will accept payment to the scriptPubKey [DUP HASH160 PUSHDATA(20)[e4e517ee07984a4000cd7b00cbcb545911c541c4] EQUALVERIFY CHECKSIG]”.
Payment to any other scriptPubKey may not be recognized by Alice.