I am currently looking to employ a freelancer in a country that currently doesn't provide CC services. He uses far older versions, so to help, I was considering paying for the licence, then giving him the logins to access his paid account. Is this achievable or will he be denied access logging in on the other end?
Due to regional differences, your freelancer really should purchase their OWN subscription. You can compensate him/her for it if you like. That said, ensure their machine meets the system requirements to run Creative Cloud + OS + all other apps you use. Check each one. - https://helpx.adobe.com/creative-cloud/system-requirements.html