Yes, I would do it again, and I would buy exactly what I bought last time (G15, 110" screen, Lexicon DC-2, HTPC, DTC-100, etc.). I think it is going to be four years before we see our first downrez'ed content, since it is going to take that long before there are enough DVI/HDCP boxes installed so that someone could make money targeting just those poeople (I certainly would not pay for any PPV event that I could not see in full HDTV).
In four years, a ton of stuff will have changed. Even though the HDCP license agreement outlaws converters from DVI to analog, it would not surprise me to see that change. Even if it does not change officially, there are a lot of enterprising entrepeneurs (especially offshore) who will happily take our money to solve these kinds of problems. As long as such a box does not facilitate piracy on a massive scale, the content providers are not going care if we buy them so that we will subscribe to their content.
There is also likely to be some legal action the first time people like me with analog inputs on their display devices are not able to watch something broadcast in HDTV. So, it would not be surprising to see court action faciliate the production of converter boxes.
Bottom line, go buy your stuff. Enjoy it.