Jeff, to just set the record straight, I think we are both still in the same crowd as I have never really made a purchase over $3K(yet). I am however maybe at the same philosophical point as you are hinting at.

I think the Heuer is a tad behind the Omega but that has been on a more historical basis due to popularity. I know this site has done a lot to even up the ranks between the two makers.

That being said, there is definetly a whole world operating above this. Like I said there is Patek and then everybody else. There are certainly many really cool watches to choose from, some with better credentials than others with prices to match. This may be the cause of our problem with collecting. Go figure why an IWC Ingenieur goes for many thousands when a simple Omega looks the same for under a grand.

A cult like following gets going and is perpetuated. I think we have given the Heuer brand a great start at that for the future, with matching price appreciation. As the cult grows and the number of devotees increases the brand prices increase due to a limited supply.

But the problem at hand is what does the sport mean to you. If your budget won't allow there are plenty of Bull Head Seikos for a few hundred dollars. The thrill of the hunt can be just as exciting. The same can be said for hunting for that special Heuer, or at the top of the market, Patek, only difference is the number of zeros in the price. Actually, there really is a quality difference, but maybe that's not why you are a collector.
I collect Heuers because of my interest in racing. Therefore almost every watch I own is a chronograph. A simple looking IWC Ingenieur or Patek for that matter just doesn't do anything for me although I appreciate the quality and history of those brands. On the other hand, my IWC Titanium GST is one of my favorites that I wear often.
So this hobby means many things to each of us. As we grow our collection and passion, so do our tastes and hopefully we will have the budget to grow with it.

Wow, that's a lot to chew on for today. Guess this helps me too as I figure out the next conquest and addition.