I asked a good friend of mine the same question when the Zipps first came out - probably 10 or 12 years ago. He looked at me and asked "Will you make back the $1000 you're spending on the wheels if you get them?"
Well, no.
But I also don't make back almost any of the money I spent on my frame, bars, seat, cranks, levers, tires, heck, even my entry fees.
So are they worth it?
They might be worth 0.5 mph at 25 mph but I don't think that's where you'll really notice the difference. You'll notice it at crunch time, when the pace has hotted up to 35-40 mph and everyone is scrambling for wheels. At that point I feel they're worth 1-3 mph (depending on how deep a rim you get). My legs feel a lot less stressed at those times. Note: I don't do road races due to lack of fitness so mainly do flatter fast crits.
Top line vs lower - probably not a huge difference in performance. The quantum leap is going to a deep rim with fewer spokes - once you're there, the differences between wheels is less significant than, say, your current wheels versus any deep rim wheel. Paying more for a deep rim wheel gets you fancy light hubs, better spokes (straight pull or not), and perhaps some patents. The expensive ones typically get you wheels which sponsor a ProTour team or has some brand name. For me, a Cat 3? I was seriously thinking of getting the Zipp FlashPoints for training. Then I saw the WilliamsWheels (the tubular would make a good race wheel I think). Both deep wheels are about $1000, my self imposed limit for not feeling like I got raped on a set of wheels. Instead of buying either I got a PowerTap - and I like looking at the data so much I decided to save up for a 24H PowerTap hub so I can lace over a Zipp 440 rim I have laying around. My rear Reynolds DV has been unraced for the last few races as I use the PT wheel instead.
The only race wheels I've sought since testing riding a number of aero wheels back to back are the Specialized TriSpokes (i.e. HED) and deep carbon wheels (Zipp 440, then Reynolds DV). I've also used Spinergy Rev-X's, a rear disk, and medium deep rims. I like deep aero wheels much I pretty much exclusively rode on TriSpokes (which were the worst for catching cross winds) for a few years so that I could ride them in any wind I saw around here.
I don't make money racing - I might win $100 a year (this year - $0 so far). I pay to race. Racing involves a lot of time and energy and money - buying equipment after figuring out what to buy, training or trying to train, driving to races, and racing itself. Fast wheels makes the racing I do a lot more fun. I'm already way into the sport. I spent more on wheels than on my frame(s) or my group(s). It's where I notice the most difference in performance. To me they're worth it.
A relatively unfit Cat 3 who isn't married yet and doesn't have kids (yet) and loves racing,
cdr