Usually you can just import the leaf self signed cert as a CA in your OS trust store and the problem goes away (assuming it has an IP SAN). Slightly tedious but you can issue the certs with long validity
Chrome provides no simple way to trust a self-signed cert. When you go to certificate details, the only option under the "Details" tab is "Export...". The only work around is to click "Advanced" and "Proceed to example.com (unsafe)". Chrome will then helpfully suffer amnesia in 1-3 days and completely forget you want to allow an exception for the certificate.