My server running on PC uses LibreSSL My client running on board uses wolfSSL Will handshake be success?
Different TLS implementations can work together because they all implement a standardized protocol. This does not mean that it will work in all cases, i.e. common problems like no shared ciphers, invalid certificates etc can happen both when connecting with different TLS stacks but also when connecting with same TLS stacks.
In other words, there are no inherent handshake problems caused by using different TLS stacks. But other problems might make the handshake fail.