OK... here it is.. the winning order. I will only modify this if urby says something like "I have tons of those already" or "I tried that and didn't like it" -- although the latter is not possible in the selection below. I set a rule for myself that I would try to stay below the $800 limit, and managed to succeed.

It should also be noted that Urbino will be announcing the winner on MY birthday. However, this should in no way influence his decision unless I would otherwise lose :)

Smoker Profile

Name: Dr. Juvenal Urbino
Location: Memphis-ish Tennessee (I don't remember)
Interests: Smoking cigars; teaching parrots to speak

Facts

Things the good Doctor knows about himself:
1. He loves Cameroon wrappers
2. He also enjoys a Maduro wrapper
3. He values a high length-to-girth ratio, in order to maximize the amount that the wrapper contributes to the overall experience
4. He is very aware of value -- if a significant savings may be had by purchasing in box, he will try to do so
5. He prefers Rocky Patel to Gurkha
6. When sampling a new cigar, he prefers to keep 3-5 on hand to experience the way the cigar changes with age

Things the good Doctor will come to learn about himself:
1. He has had more than one Sumatra-wrapped cigar in his lifetime
2. The Sumatra leaf creates his favorite flavor profile
3. He prefers a Sumatra wrapper leaf grown in Ecuador over Cameroon

Analysis

Dr. Urbino believes himself to have had only one Sumatra-leaf cigar (Oliva Special S). However, one of his personal favorites (Rocky Patel Vintage 1992) is wrapped in a Sumatra leaf grown in Ecuador. The Cameroon wrapper tends to add a zesty spice to the flavor, and an Ecuadorian Sumatra creates a fuller, richer, smoother flavor. The maduro leaf tends to be smoother still, but less rich than the Ecuadorian Sumatra. Dr Urbino is well-educated in the realm of premium hand-rolled cigars, but he is suffering from a mild experience gap with respect to Sumatra cigars.

Conclusion

In order to help Dr. Urbino take the next step in his cigar smoking education, he needs to experience a tour of premium Sumatra-wrapped cigars, supplemented by a healthy offering of high-quality Cameroon and Maduro cigars. In order to optimize the experience of the wrapper leaf, these selections should be chosen with a healthy length-to-girth ratio. Given the parameters of our budget, I prescribe the following:

Rocky Patel Vintage 1992
Wrapper: Ecuadorian Sumatra
Size: Churchill (7 x 48)
Quantity: Box of 20
Cost: $139.95
Reasoning:
This is a staple in Dr. Urbino's inventory, and he trusts it as a stick that consistently delivers a rich flavor. The box purchase offers a savings of $1/stick, which isn't exceptional, but for a cigar this good, it's still a bargain.

Montecristo Serie C
Wrapper: Cameroon
Size: Toro (6 x 54)
Quantity: Box of 21
Cost: $149.95
Reasoning:
This selection, also from Dr. Urbino's self-prescribed list, features a premium cigar wrapped in a Cameroon leaf. The savings for a box purchase is a whopping $1.86/stick, bringing this to a similar cost/stick as the RP Vin 1992. While this cigar carries a larger girth, the Montecristo filler tobaccos are recognized in the industry as a high-end standard, and this cigar will change and improve dramatically as it ages.

Graycliff Original Release (1997)
Wrapper: Sumatra
Size: Coronas (6 x 38)
Quantity: 5 singles
Cost: $65.00
Reasoning:
Dr. Urbino selected this from the cigar.com aging room as a premium treat, and a branch out into the world of Sumatra-wrapped cigars. The length-to-girth ratio gives an excellent opportunity to live the full experience of a super-premium Sumatra wrapper. The box purchase is both expensive, and does not offer a very large savings over the single stick price. This should be a glorious special-occassion smoke.

Montecristo Media Noche
Wrapper: Maduro
Size: No. 3 (5.5 x 44)
Quantity: Box of 20
Cost: $114.95
Reasoning:
Dr. Urbino had chosen this brand as a candidate for his birthday purchase, but he would prefer this in the size I have prescribed here. This cigar features a Maduro wrapper, and would be a wonderful smoke on a cool, clear afternoon in the early fall. At a savings of $1.75/stick, the box purchase is practically stealing.

CAO L'Anniversaire Cameroon
Wrapper: Cameroon
Size: Churchill (6.8 x 48)
Quantity: Box of 20
Cost: $138.95
Reasoning:
From this point forward, all the recommendations are originals, not featured on Dr. Urbino's list. This stick features an excellent length-to-girth ratio, and is, in my opinion, one of the better Cameroon cigars out there. This box could be substituted with a CAO CX2, but I haven't had that one to make a good comparison.

La Flor Dominicana Ligero
Wrapper: Ecuadorian Sumatra
Size: 400 (5.7 x 54)
Quantity: 5 Singles
Cost: $23.75
Reasoning:
Now we're getting into it. This recommendation begins Dr. Urbino's official entry into the world of Ecuadorian Sumatra wrappers. This full-bodied cigar is so pant-crappingly tasty, Urbino will hang himself for only ordering 5. At that point, I just hope he willed me his entire Ecuadorian Sumatra collection.

Arturo Fuente Sun Grown
Wrapper: Ecuadorian Sun Grown
Size: Chateau Fuente (4.5 x 50)
Quantity: 5 Singles
Cost: $28.20
Reasoning:
As Dr. Urbino adventures into this new territory of the Ecuadorian Sumatra cigar, he will find himself wondering what it is about Ecuador that makes the Sumatra leaf that much more appetizing. Well, a great way to experience this is to complement the selection with an Ecuadorian Sun Grown beauty from the likes of Arturo Fuente. With the smaller size of this cigar, it will be a perfect afternoon or early evening smoke on a 2-cigar day, perhaps followed by a Sumatra or Ecuadorian Sumatra cigar to compare and contrast the differences.

Trinidad
Wrapper: Ecuadorian Sumatra
Size: Corona (5 x 44)
Quantity: 5 Singles
Cost: $40.00
Reasoning:
What is this, you say? This cigar hasn't gotten any mileage or attention on these boards. Where did this come from? This, my friends, is the pinnacle of this recommendation. The ultimate prize in a most glorious birthday. The Trinidad cigar, in its Ecuadorian Sumatra wrapper, is a King among Kings on this ticket. This cigar is a rich experience, and an ideal candidate to learn about this wrapper as it ages.

Gran Habano VL (2005)
Wrapper: Maduro
Size: Churchill (7 x 50)
Quantity: Box of 15
Cost: $74.95
Reasoning:
This is an extremely rare Maduro, and a second entry from the cigar.com aging room. At a savings of $1/stick, the Box of 15 doesn't offer a huge savings over the individual stick price, but the rarity of this beauty ensures it will be a great special-occassion smoke or a one-of-a-kind gift to a good friend.

Sol Cubano Sumatra
Wrapper: Sumatra
Size: Churchill (7 x 50)
Quantity: 5 Singles
Cost: $17.50
Reasoning:
We're just about out of room on our budget, and we need a classic Sumatra wrapper to help compare and contrast against Ecuador in our Great Sumatran Tour. I'm not sure if Dr. Urbino has sampled the Sol Cubano Sumatra yet, but it's one of the better-valued Sumatrans around, and one of the few that will keep us within our budget of $800.

So.. there you have it. 121 cigars for a total price of $793.20. But wait, didn't I promise that the order total was $798.20? I did indeed. I would be remiss if I left out the Cuban Hertage Sampler from cigar.com. This features a Montecristo, Romeo y Julieta, and a Fonseca Habana Seleccion, all for the total price of $5.

Total Cigars: 124
Total Cost (before shipping and discounts): $798.20

Option:
If Dr. Urbino has already sampled (or has sampler on hand) the Sol Cubano Sumatra, I would like to substitute the following recommendation:

Flor de Oliva
Wrapper: Sumatra
Size: Churchill (7 x 50)
Quantity: 5 Singles
Cost: $12.50
Reasoning:
Dr. Urbino is very familiar with, and enjoys, Oliva cigars. This is a value-priced, Sumatra-wrapped cigar from the Oliva family that would be an excellent candidate for an everyday smoke. Also, at the slightly lower price of these five sticks against the Sol Cubano Sumatra, Dr. Urbino now has an extra $5 to spare and spend on the "5 for $5" sampler -- at a buck a stick, how can you go wrong with that? This substitution preserves the overall price of $798.20, and adds an additional 5 sticks for a total of 129.

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A. De Mello:

There is not a single moment in your life when you do not have everything that you need to be happy.

if this doesnt win i quit life. also if i ever want to place a hudge order ill just give the money to duty and let him analyze me

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If you are going through hell, keep going.
Winston Churchill

Jesus H.

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Buffalo buffalo Buffalo buffalo buffalo buffalo Buffalo buffalo.

dutyje:

However, one of his personal favorites (Rocky Patel Vintage 1992) is wrapped in a Sumatra leaf grown in Ecuador.

I did not know that. The descriptions always just say "Natural wrapper," which never made sense to me because it certainly doesn't look like any natural wrapper I ever saw.

I gotta say, guys, duty has set the bar damn high.

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Buffalo buffalo Buffalo buffalo buffalo buffalo Buffalo buffalo.

Thanks urbs.. I got the skinny on the RP Vin '92 from the Rocky website. The writeup on cigar.com says it's grown in Ecuador, but they don't tell you it's a Sumatra seed. There are openings for improvement in the order I proposed, though. I could make a couple minor improvements, but I wanted to stick with what I had promised this afternoon, and the alterations would probably put me a few bucks over the limit anyway.

Cigar.com doesn't carry them (yet), but I have to say you would enjoy the new Playboy cigars immensely. They feature an Ecuadorian Sumatra wrapper as well, and must be one of the greatest cigars I've ever had -- and easily the biggest surprise I ever smoked.

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A. De Mello:

There is not a single moment in your life when you do not have everything that you need to be happy.

Yeah, I've had that one in the back of my mind since you praised it so highly a while back. Haven't run across any yet, but it's on my list.

I really should hit more of the makers' websites. I think Fuente is the only one I've visited.

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Buffalo buffalo Buffalo buffalo buffalo buffalo Buffalo buffalo.

i logged on to post my selection but i have no chance now.

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Kuzi's cigar catalog blending 101 developing your palate

Nooo! Don't say that. Post it, please. I mean, you've already taken the trouble to put it together, you might as well post it.

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Buffalo buffalo Buffalo buffalo buffalo buffalo Buffalo buffalo.

urbino:

Nooo! Don't say that. Post it, please. I mean, you've already taken the trouble to put it together, you might as well post it.

Ummm urbino, duty just made my dream list right there. Thats going to be my birthday order. I agree with duty too, I like the Ecuadorian Sumatra more than the Cameroon, as of right now. But the CAO L'anniversaire is excellent its a single cammie though instead of a double, hence Cx2.

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CONSULTING:
If you're not a part of the solution, there's good money to be made in prolonging the problem.

madurofan:

Ummm urbino, duty just made my dream list right there.

No kidding. Now I have to figure out a way to ferret $800.00 away from the bank account without the wife finding out >.>

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"Sometimes I think that the surest sign that intelligent life exsists in outer space is that none of it has tried to contact us yet."

Calvin, speaking to Hobbes

Impressive as duty's list is, and the tremendous amount of effort he put into it, there are some things I would change about it.

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Buffalo buffalo Buffalo buffalo buffalo buffalo Buffalo buffalo.

I've got a re-worked list that I think is a pretty nice improvement/alternative, taking care of what I see as the only flaw. I'm going to stick to my guns on my original, but I'll post up a revision after this thing is over. Surely some of these super-knowledgable cigar freaks (kuzi, maddy, kas, jozer, smoke...etc, etc...) can take it to another level. I also have to say jozer's original list was pretty amazing as well.

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A. De Mello:

There is not a single moment in your life when you do not have everything that you need to be happy.

duty I don't even wanna try to compete with that.

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CONSULTING:
If you're not a part of the solution, there's good money to be made in prolonging the problem.

dang, man.. I'm flattered

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A. De Mello:

There is not a single moment in your life when you do not have everything that you need to be happy.

madurofan:

duty I don't even wanna try to compete with that.

i concur

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If you are going through hell, keep going.
Winston Churchill