Entitlements affect everybody, so you need to reach out to both sides. Everybody has to be brought along as much as possible. Or else there would be animosity and distrust.
Yes we do have the general election votes of the Greatest Generation versus Democrats - but that only goes but so far. We don’t have the votes for reform on our side. Not even conservative Republicans will bring any serious entitlement reforms to the floor of Congress. Therefore the need for outreach.
First off the “greatest generation” is what, older than 88 or 90 years old?
I think your problem is convincing the age group that won’t vote republican to start voting republican.