Tim,
This is something one has to do in order to know just how "bad" the timing can get. Obviously, one has to specify the worst possible timing in order to have a design that works.
If one logic block (let us be generic here) is slow, and it is slower than what you thought it was going to be when you made your speeds file, then that chip might fail to meet timing on that path, and you get data errors.
How you go about finding the worst of the worst on a die is something that we have to do, so that we can be sure we are OK when we ship the part to the customer.
A ring oscillator is a very useful thing to do this, as measuring frequencies is often easier than measuring delays. There are other ways to do this, also.
Whatever, we have to do this in such a way to meet the quality objectives, and the cost of testing objectives at the same time. This is yet another reason why Easypath(tm) devices can be much lower in cost: we only need to test the paths you use to meet timing, not every possible path. It is also a reason why ASICs (structured, or otherwise) might have very poor yields all of the sudden (known as a 'yield crash' in the business)! If your ASIC has a yield crash, you may only be affected because your supply of chips disappears, but if you are paying for the wafers, then you will be doubly punished.
There are papers on this subject (search IEEE, etc.) as well as papers yet to be published on the subject.
This is one more reason why using a FPGA device takes a lot of the work out of what you would have to do otherwise with an ASIC: we do the hard work so you don't have to. We also remove substantial risk (yield, performance-timing closure, latchup, single effect upsets, etc.).
Every one of the risks above is documented fact for some structured ASIC suppliers. That means each one has already happened to at least one customer! This is one of the reasons why the structured ASIC business has more companies that have tried it and left, than those that are still struggling to make a go of it. Don't forget that Xilinx, too, was once a 'structured ASIC supplier' (HardWire(tm) devices). Been there, done that, learned our lesson.
And yes, as things have gotten smaller, the variation has reared its ugly head. Learning to live with the variation, or prevent it in the structures that you care about is no easy thing to do. Identically drawn devices, next to each other, can vary by +/- 20% in some cases. Try using devices like that to match something at all! The good news is that we IC designers "have ways" to meet our objectives.
Austin