Thoughts about CDs always trailing inflation? Sure. You won't stay ahead of inflation with CDs. You buy CDs for the safety -- FDIC insurance. Inflation isn't the issue with CDs. It's the interest rates. The bank is like a casino -- it's always going to make money.
If interest rates go up, so will CD rates, but the bank will stall raising them as long as it can without losing all its customers. If interest rates are falling, the bank will be right there lowering them immediately. The ladder just protects you from a catastrophe when interest rates are rising. You don't end up sitting there stuck with a big chunk of your money in a 4% 10-year CD while you watch interest rates skyrocket to say 18% (and inflation go wild). Think it can't happen? 1970s. The ladder also lets you keep the higher rates a little bit longer when rates are falling.
So how can you win with CDs? Same as with gambling -- by being lucky. By grabbing a huge long-term CD when interest rates are high, right before they drop like a stone. Is there a chance you can do that today? No way, interest rates are incredibly low from a historical perspective. Rates are so low, it doesn't make much sense to get a long-term CD right now even in a ladder situation.
Where you get inflation protection is from TIPS and I-Bonds ,where the interest rate can actually INCREASE periodically based a number from some inflation index. With I-Bonds you get a base interest rate which is fairly low, and the inflation rate gets added on to that. You can cash the I-Bonds out after a year with a small interest penalty if you need to. I've got some I-Bonds from 2002 where the rate is 6.89%.
I don't see why you are making life complicated for yourself by trying to figure out the TIPS secondary market, especially after Scott recommends against it. If you have enough money, start a TIPS ladder from Treasury Direct and hold them until they mature. If you haven't got enough money for that, buy I-bonds. Otherwise buy a fund of TIPS. Now go out and enjoy the sunshine.