To answer the first point, here's a comparison of the <Realm>
from my context.xml before and after the switch to Tomcat 8:
Before:
<Realm className="org.apache.catalina.realm.DataSourceRealm"
dataSourceName="jdbc/myDataSource"
roleNameCol="role" userCredCol="password" userNameCol="loginid"
digest="md5"
userRoleTable="userroles" userTable="users"
localDataSource="true" />
After:
<Realm className="org.apache.catalina.realm.DataSourceRealm"
dataSourceName="jdbc/myDataSource"
roleNameCol="role" userCredCol="password" userNameCol="loginid"
userRoleTable="userroles" userTable="users" localDataSource="true">
<CredentialHandler
className="org.apache.catalina.realm.MessageDigestCredentialHandler"
algorithm="md5" />
</Realm>
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