Telecaster: I actually think you proved the point from the value investor's perspective, not the indexer's. You cleverly pointed out how much of a genius Frodo was for accumulating during an under-valued period ("Frodo spent more than a decade buying stocks at a P/E of 10 or less") and how great the performance was when he stopped investing ("And just as he retires, the market takes off like a rocket! Frodo sees his portfolio explode with double digit returns year after year after year.") This a direct result from buying VALUE, not everything all the time. I'm not quite sure how this helps the "index at all times regardless of valuation" argument. I don't know how so many people seem to miss this correlation. The complete opposite was just as likely to happen in the reverse scenario (accumulate during 20 year overvalued period, then retire and the market shoots down like a rocket and stays there and you are screwed). The market reflects value over time. It can stay crazy high or crazy low for long periods, but in the end, it always reflects earnings performance. If you don't believe this, I don't know how you are investing. You must have some belief that regardless of any fundamentals, stocks just go up because they do. That is called faith. It has no place in investing.
Interest Compounder: I haven't done that chart thing because it doesn't further the discussion. Value is not relative. It is objective. What you're asking me to do with that chart is pick times when I thought the market was relatively overvalued or undervalued based on historical valuations.
Here is my answer for the Shiller PE. I think a Shiller P/E of 15 to 16 is fair right now. A P/E around there implies a return of around 6% to 7% without dividends. This is based on earnings, not some relative measure. You also have to take the interest rate environment into account as well as corporate profit margins and judge within that context. Typically, I think the average investor should shoot for 4% to 5% above the risk free rate. Right now the 10 year T-bond is 1.81%. So I'm looking for a 6% or 7% return right now for stocks, which equates to a Shiller PE of 15 or 16. Since the Shiller PE is 24.4 right now, it is over-valued, especially with sustained high corporate profit margins. If corporate profits revert back to the mean, which they have done for the past 65 years, the Shiller PE would likely be in the mid-30's.
For the Buffet Indicator: This is total market cap divided by GNP. Simply put, it is a measure of the size of the stock market compared to the size of the actual economy. Right now it is at 109%. So...the stock market is 9% bigger than the actual economy. It is overvalued. You are paying 9% over fair value when most smart investors should be looking for a 25% margin of safety aka a Buffett indicator percentage of 75%. Don't believe me, here's what Warren Buffet has to say about it, "If the percentage relationship falls to the 70% or 80% area, buying stocks is likely to work very well for you. If the ratio approaches 200% -- as it did in 1999 and a part of 2000 -- you are playing with fire." So yeah, the world isn't ending, but indexing the whole market is not a great idea right now if you are investing for the long-term.