Didn't really open it up. Only $100 worth of Cuban tobacco allowed to be brought back during travel.

Montecristo Afrique Jambo (first impression):

Oh man, just tried a Montecristo Afrique Jambo. Kicked my butt! Oh gawd, the nicotine nausea and lightheadedness. I don't even inhale but will occasionally take in some second had off the nose for aroma's sake. This thing is the strongest cigar I've ever smoked in pure nicotine power, and this was with a full stomach. I could only make it through an inch and a half before I had to stop otherwise pass out. Wow. Could be me and/or the cigar. Will have to revisit at a later date.

Wrapper is supposedly a vintage Cameroon which I don't doubt since it was less sweet and sucralose tasting like more modern Cameroons. Fillers are Nicaraguan, Peruvian and possibly Tanzanian as well from what I could gather. Straight away upon lighting it had a more old school and unique and sharp earthiness I recall from late 90's tobacco which reminded me of some Partagas Cifuentes I used to smoke back in the day. That was a welcome surprise. Definitely an earth (not dirt like some modern earthy cigars), char and black pepper on the palate. I thought what little I was able to make it through was pleasant enough and brought back some old memories so it worked out though short lived. The burn and draw was just right for my tastes also.

I'll revisit it again and likely do a comprehensive side by side comparison versus the CAO Columbia which is another Cameroon but with a new breed of Columbian and Brazilian filler (assuming the power of this sample parejo was an outlier). 

Boy did I get pwn'd. 

Any recommendations for where to start with cigars?

TLDR:

Grab an original My Father Robusto for quality construction and flavor. See how that works out for ya. Make sure you slow roast the foot gently till the whole bottom turns cherry red (when you blow on it) before you snip the cap. That's how I do it. You don't want to char the tobacco and let that nastiness carry throughout the cigar and pollute it if that makes sense.

I have no idea how to take the properties of what I do like and find that in another cigar I haven't tried. 

Construction and composition! Look at what is used for the wrapper, binder, filler, and how and where the tobacco is grown, I tend to find myself trying a cigar and noting various flavors or attributes telling me which region the cigar came from and what wrapper, binder or filler is being used.

For example, Cameroon wrappers have a very refined sweetness that's borderline like a processed sugar. Ecuadorian Sumatra has a sweetness but is deeper and richer than a Cameroon bringing floral, caramel and sometimes fruit notes. E. Habano is an earthier, more leathery, earth, with some nut and wood flavor. Connecticut is a very classic mild nut and wood without the deeper leather and earth. Maduro is a more espresso, chocolate tasting wrapper tat can vary widely depending on whether it's a Padron maduro or a typical St. Andres maduro from Mexico. A green candela is sweet but has a more robust sugar than Cameroons with an herbal undertone.I love a good high quality Honduran Corojo as they hit a blend of Cuban Habano triggers for me. Then you have sun grown, shade grown, high priming and mid/lo priming leaves. The debate about the merits of ligero and non-ligero fillers, etc., etc. Some also feel a wrapper with more tooth and texture will provide a heartier and more robust flavored smoke.

Also the shapes of the cigar will dictate which leaves will be used and how they will be composed in that particular model and shape. Different sizes can usually have their flavor profiles within the models in question. It's really all simple chemistry and physics of how ratios change and are subject to varying enthalpy (thermal change and combustion properties).

Water content is also a seriously big deal which affects all the above. The level of humidification and rest time is crucial. Water affects the rate of burn and flavor profile. I tend to find when humidity is too high, the combustion process seems to add bitterness to the cigar wrecking it. It also makes it harder to stay lit. You also cause the leaves to swell and potentially crack. Too low and the flavor and sweetness gets neutered, and once again cracking of the wrapper. You want that perfect balance which for me is around 65-68% depending.

So look at the cigar you like and learn everything you can about it. Then try to find something as similar as possible and note any differences as they variables change.

Thanks for the primer!  I'll have to keep a note of what properties I like to research others.  I guess I should find out more about Ecuadorian Sumatra.  Truth be told I've never tasted a difference in shapes, but I probably don't smoke enough to be able to notice.

Interesting, this is the first I'm hearing about resting cigars.

I noted that if I buy a VSG and smoke it right when I get home that it tends to taste a little off.  Maybe too acrid.  I had no idea what to chalk this up to.  When I let it sit in my humidor for a while, I like the taste better, it is less acrid and sweeter.  I found this counter intuitive because my humidor isn't very well regulated.  Not being a huge collector I only keep 6-10 at a time and my humidor and humidifier are pretty low rent.  I don't measure the humidity, I just refill the liquid on a periodic basis.  To me it seems like the cigar should have its best humidity coming straight from my cigar shop's humidor. 

It's entirely probable it does have its best humidity coming from the shop, and maybe my palette / preference is unrefined. 

Yeah, particularly if you compare a Gordo to a Lonsdale or Corona. Not only does the size change what size and picking of leaves the rollers use, but it changes the ratio of wrapper to filler leaf. Many say the wrapper accounts for 70% of the flavor, I think it's closer to 55% and it's really dependent on how you smoke since your nose affects your palate. I don't try to inhale or retrohale myself, though sometimes the second hand is so delicious it's hard not to take a sniff. That's not quite as bad since the temperature is lower producing less combustion by-products.

On the resting, I find B&M stores to over humidify for my tastes. I agree that often smoking right from the store often yields an acrid and less than pleasant experience. Part of that, particularly with shipped cigars, is the shock and disparity of the internal humidity and temp to the external environment as it's trying to constantly equalize. What happens is you can get an unevenness. It's essentially a living plant still to degree. It's physical structure adheres rules of diffusion and fermentation is persistently ongoing. It you smell hints ammonia from a cigar or a humidor that's the fermentation cycle still ongoing. Resting is a great way to just give it a day or two for the cigar to stabilize. Their is also something called dry boxing. If you find your cigars over humidified or acrid sometimes, just put the one you want to smoke in an empty old cigar box in a cool temperate room for a few days to a week and then try it. You might notice a difference.

How fast and how hot you get a cigar also can yield a burnt and bitter taste. There's an ideal temp at which you want to light and smoke tobacco. For example, think of the sugars in BBQ sauce. You want to finish with the sauce at the end of your grilling or smoking so the sugars don't burn and wreck the meat. You want just enough heat for the sugars to caramelize, but not burn (which is usually above 225F). Same with the sugars in tobacco, which is why it's ideal to slow roast the foot of a cigar with a low flame rather than blast it with a flame thrower till it turns to ash.

I think smoking straight from a shop yields a poor set of external conditions for a cigar. You have instant gratification so one will be impatient getting that thing going. If it's overhumidiifed you'll put more heat to the cigar for longer and chances are you had the store cut the cap off before l ighting if you don't have your personal gear on you.

The size and shape of your cap cut can also affect your flavor due to changes in air flow and burn rate. I've also seen small punch cuts sometimes concentrate tar to the point it starts oozing out the end wrecking the cigar (rare but nasty). I use a double guillotine for Figurados and a double V-cut in a cross pattern for others. That's all another story though.

Again, this is all IMHO and IME. YMMV.