<Well, if the govt has to cut a check for education, then how does it differ from social security? A federal check is a federal check, isn't it?

Absolutely right. Spot on.

In an ideal world, people would purchase education like they would purchase food, cars, homes, electronics, and everything else that is so superbly provided by the private sector. Maybe the poor would be subsidized in some way, in the same way that food stamps subsidize food purchases, but the grocery stores are still part of the private sector.

In an ideal world, people, or the companies they worked for, would manage their own retirement savings. Again, with a possible subsidy for the indigent (A means-tested Social Security benefit of some kind?)

In an ideal world, "entitlements" would be recognized as simple welfare, or wealth transfer, and would be avoided in favor of other solutions.

Since we don't live in an ideal world, but the real one, and there will be ski-jumping in Hell before Social Security or our education system are privatized, we work with what we have to at least increase the options of the citizens.

Vouchers increase the options in education. Being allowed to invest some of our Social Security funds as we see fit increases our options in retirement. It's better than a poke in the eye with a sharp stick.

Being willing to accept a small ratchet away from socialism and toward freedom is not hypocritical, which I gather is what you're trying to imply.