I’ll do a bulk response here to save some time. It's still a long response. First, thank to everyone for their wisdom, great suggestions and interesting debate points! Here is where I’m leaning, but still need to do lots of testing and deciding.

I will be test riding the Co-motion Supremo Co-Pilot, a Calfee Dragonfly and maybe a Co-motion Speedster tomorrow. Now, that sounds like a fun “work” day.

Couplers: On the bikes being tested the delta on price for couplers is about $2,000. SS on the Co-motion and Al on the CF. I believe that most who commented on the “local” travel not needing couplers is the right and an economical decision. I have a trunk rack for our two singles today (can fit 3). The tandem would fit fine, with the front wheel removed. I drive an older V70 Volvo, so it’s big enough. Roof-rack is also an option for road trips (will remember to put just the bike on the roof-rack [wobblyoldgeezer].

The issue is on air travel. We plan (hope to) to do some trips to Canada, Europe and other places in the US. From what I have learned the airline policy and practice is all over the place. For a full tandem you could get charged anything from $40 to $400 per trip. And what they tell you over the phone is not the same as what the practice at the counter. Then there is the challenge of car rental when you get to another location. They don’t (generally) do bike racks and definitely not tandem bike racks. No too many option on large vehicle rental in Europe unless you want to deal with the parking challenges also. The cases make it easier to handle. The cost and the assembly/disassemble are the big drawbacks. Cases (need a pair) go from $500 (soft) to $1,000 hard. Say $3K. That would be an 8- 75 trip payback!! I’m sure airlines are not going to get easier, as the look for every way to make money.

On the touring type [WebsterBikeMan] it should be credit card or fully supported. Looking for the American Express Black card At this stage of our life, our idea of roughing it, is the Holiday Inn or Formule 1 (France). Great advice on the CF limitations on racks, although I saw a Calfee well outfitted for self-contained touring (somewhat) - http://www.thetandemlink.com/calfee_tandem_12.html
Brakes: I’m a speed demon – regularly 50+ on a single on Passes – Fremont (N), Loveland (S), etc. My stoker probably never goes past the 30s. But, she enjoyed it when we did the tandem test and wanted me to go faster!! There appears to be tandems with three sets of brakes – front, rear and drum!! The thought of two people being capable of breaking (other than an extreme emergency), scares me [reversegear]. I’ll take the punch in the back instead. For all the big climbs/descents in Colorado and the ones we hope to do in Europe (Alps, Pyrenees), I think the advice of a disc in the rear (Avid BB7 Road w/203mm G2 Clean Sweep rotor – thanks [TandemGeek]) and Shimano calipers in the front sound good. A drum appears to add too much weight for the limited use.

Performance: On the drive train it looks like Ultegra is a good compromise between shifting capability and wear (thanks [pablopsd, WebsterBikeMan]). I love my D/A (lighter, smooth shift), but they do wear faster.

Comfort: Will do the carbon versus steel test drives. A CF fork appears to be a given on a steel frame [rdtompki, zonatandem]. We will test the stoker comfort with a regular seatpost. I’m definitely told to have a Thudbuster with aluminum. But we are going to stay away from Al. Thudbuster is still an option [swc7916, rdtompki]. I’m good with road hazard notification, but you always miss something (I hate valve covers that blend with the pavement. They come in packs!!).

Wheels: The trade off of performance versus comfort. Are the Rolf really uncomfortable [HowellGC] and versus what other wheel set(s)? I will test both. I ride on Mavic Kyserium SSL on my single.
Sizing: Thanks for the guidance and the sizing link [WebsterBikeMan]. Looks like a small or medium. I’m 5’ 9” (1.75m), inseam 83cm and my wife is 5’ 2” (1.57m). I like to be stretched out. My stoker does not. The life of compromise! Not sure we are up to the Robusta/Macchiato standard [merlinextralight]. Need to lose a few pounds and get back in shape. Seems like a young couples challenge. We are going the wrong way, age-wise, speed and climbing ability. No Robusta/Macchiato at LBS.

General: I like the idea of a wireless intercom [rdtompki], do deal with the issue of wind noise and hearing (or is that heeding!) issues. I saw a Blue Ant InterPhone (Australian) recommended somewhere. Very light, can deal with 80MPH wind noise (built for motor bikes), but only has 5 hours of battery life.
Definitely will not do the TripleByPass as the first century [zonatandem]. Did it a few times in well under 8 hours. There is no hope of doing it in anything near that on a tandem.

Descending Mt. Evans [oldcura] probably needs disk or drum brakes, but definitely a Thudbuster!

Price: Cost is always an object [TandemGeek]!! Still waiting for the PowerBall to come in. I’m not sure it’s quite the 3X price challenge of a single [WebsterBikeMan]. My current single as outfitted was in the $4,500+ range, but I get your point. Carbon, couplers (e.g. Calfee Tetra S&S) with top end components can get you to $13K quickly.

The ultimate and biggest challenge. Do you go for the dream machine now or work up to it over a number of years. My wife’s experience on her single would says no. Then again we are tandem novices. Thanks - [DKMcK]

I have looked at Craig’s List and just missed a Co-Motion Supremo (couplers and all the goods) in Highlands Ranch for $6,500 a few weeks ago (New $9,000+) about a month ago. Did not see the one in Vail [oldcura]. Will continue to look. There are some options on 2008 stock that is $500-$700 less than 2009 for Speedster and Supremo models. Looks like we should look at Cannondale too [pablopsd, DKMcK]. Need to find more dealers.

But now off to the LBS, tomorrow. I will update on my experiences.

Local Dealer: Yes, it wonderful having a local dealer with stock and they apparently ships bike all over the place. Patrick and Lynn at Tandem Cycle Works [zonatandem] have been great.

It's all downhill from here