More about talking to Social Security

Now, I know part of the problem is with me.  To their credit, after Monday, I was able to contact the Social Security people without a long wait time... that is, AFTER I spent at least ten minutes talking to the robot.  I actually contacted them three times yesterday and once today.  Why so many times?  
The first guy I spoke with about starting Cliff's Medicare said he would have to talk to Cliff, personally.  Since Cliff was still asleep, I thanked him and hung up.  
Once Cliff was up, I called again.  
Now here's the thing:  at first you reach a lady robot telling you something about some Obama program that started in March.  I should have it memorized by now, but I've tuned it out.  
The next lady robot tells me to say what I want, and I usually start with "Medicare signup".  Then she has to say something like this:  "It sounded like you said Medicare; is that correct?"
Of course, I say "Yes."  
Then she spends about five minutes telling me stuff about Medicare that I already know, and suggests I visit their website.  Now, during all this, I can press "O" as much as I want, and nothing happens.  But there comes a time when I hit "O" and she says, "Did I understand you want to speak with a representative?"  
"Yes," I sigh.  
She proceeds to tell me all the various ways I can find out about Medicare without speaking to someone and then says, "Do you still want to speak to someone?"  
"Yes."  
So now I am told the wait time is less than one minute.  Do I get to talk to someone that quickly?  
Oh no, the robot is back with some questions:  Cliff's social security number, the state he was born in, his first name (spell after you say it), his last name (spell that too), and his mother's maiden name (spell that too).  Whew.  Of course, she has to repeat each of my answers back to me, very slowly.  
I go through this Every.  Single.  Time.  
So Cliff got up and had a cup of coffee, and I went through the whole routine again.  This man did not need to speak to Cliff (HUH?).  He gave me three options:  1.  He could make us an appointment with the local office,  2.  Cliff could talk to someone and enroll on the telephone, or 3.  We could do it online.  
I first said let's do it now on the phone, and he told me he'd have to direct me to someone else and the process would take about 45 minutes.  And he began pitching the online route.  He explained where to go on the web, and what to click on.  "It's really very easy," he said.  
Finally, I agreed to try that.  
I will tell you truthfully that it indeed was easy.  When I was done, I printed off what I'd sent them and gave it to Cliff to read.  
"This isn't right," he said when he got to the second page.  "I'm not covered by a group health plan through my own employment."  
I had misunderstood the question and given the wrong answer.  Now what?  
This morning around 5 AM I decided to call my robot lady friend so I could talk to a real person and tell him or her about my mistake.  I went through the whole ten or fifteen minute routine with  robot with whom I have now formed an intimate relationship, and finally my real person answers.  I told him about my problem.  
"We'll have to speak to Clifford directly," he said.  "Once we get his okay, we can send the correction to the local office."  
Of course, Cliff was asleep in bed.
Dear Lord, I have to go through all that again?  Somebody just shoot me.