Doesn't "entitlement" have a bad connotation? Is that my imagination?
Are we supposed to feel guilty for collecting our "entitlement"?
No, you aren't supposed to feel guilty.
The "problem" with these types of programs, IMO, that they start out well meaning enough and then people/groups start tacking them onto things they were never intended to cover. You add a few small groups here, add a few more there, waive a few of the requirements for this group.. All of a sudden you have added a lot of people who are now entitled but the system was never designed with those added people in mind and the funding is never corrected to account for them. Then people shake their heads and wonder why things didn't work out like they were told it would when they supported it.
I should add that "entitlement" was given a bad rap in the 1970s/80s. At the time there were a lot of social programs (that all had a good purpose) that were seen as being heavily abused. I worked in a factory at one point and the Union decided to strike so we all just didn't show up at work and collected unemployment while we were on strike. IMO, it's crazy to pay people unemployment when they have a job and refuse to show up for it. That was one of many reasons for the overhaul of the unemployment rules when Reagan got into office. But yeah, overall the word picked up an undeserved negative connotation.
How do these kind of things -- government pensions -- figure into the whole SS thing. Or is that something else entirely?
There are a few different types of government pension programs so it depends on which one teh individual is a part of. For military - they pay into SS while they are on active duty so they are earning points toward SS retirement just like anyone else. The problem there is that SS Retirment is set based on how much you earned over your working career and military folks tend to be toward the bottom end of that.
For Federal Civil Service people that were on the old CSRS system (prior to 1982 or so..) - they never paid into SS and don't collect from it. Current Federal Civil Service employees pay into the FSRS (I think that's the moniker) and a portion of that monthly payment is their SS contribution so they are in the same SS system as everyone else. They both also get a monthly pension check similar to what was the standard in the corporate world up until the early 1980s.
Your brother for example, will get his military retirement check plus SS when her reached retirement age.
Some state and local level government agencies were able to exempt their employees from SS entirely so they are on their own.