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When my then 18 yr old daughter was traveling around the world, I got Amex and Visa to issue a second card in her name. Have it set up where you can pay his visa with funds from your bank account on line.
(Of course my son thinks this is a great idea--he can rack up the charges while mom stays home and pays the bills!
) I also plan to open a joint bank account with him and he'll take the ATM card.
I'll deposit money as needed, but will keep the balance pretty low in case the card gets stolen and the account hacked. The simple answer to your first question has to be a flat no.
Establish a link to these on the internet and keep track daily of what is going on.
What you DON' T want to have happen is him be stranded with no means to get out.
I noticed during my last two trips to Europe that merchants took extra care in checking/matching signatures/names on the card.