Welcome to the hobby, cigars have been in my life much longer than chipping so here's an area I can actually help!
There are some big ones like neptune and JR, they have a lot of stuff but there's a huge amount to look through and it can be overwhelming. You'll find pricing varies across wherever you look, more boutique places have slightly higher prices but its worth it for the selection and custom service. To that effect, I am a fan of smallbatch, fox cigars, and cigars daily.
So here's an important lesson. Because of the American embargo on Cuba, there is a strict distinction in America between Cuban cigars and all other cigars. Those pictured above, and available from ihav, are cuban Romeo y Julieta (RyJ). What you would have bought in an American cigar shop will 99.99% be a non-cuban ryj, which are almost all made in the Dominican Republic. For ryj in particular this can be seen on the band:
https://cdn.shopify.com/s/files/1/0...ryj_reserve_real_toro2_1200x.jpg?v=1600500317
https://www.holts.com/clubhouse/sit...mage/headerimage-DiffBetweenCuban_Dom_RyJ.png
Notice the "Habana, Cuba" on one of the bands. There are many other brands like this with a Cuban and non-cuban line (such as Montecristo, Cohiba, etc etc etc). Cohiba is an example where there is no relationship between the two companies other than shared name.
In general, Cuban cigars are generally "higher-shelf" or "better." I certainly like them a lot, but its a different world and different flavor profile and don't be misled, there are hundreds of incredible cigars not from Cuba.
Cigar tobacco is classified in many different ways. I won't get into them all here but what's relevant at the moment is that there's 3 primary pieces of information that are useful for "reading" what a cigar is:
-The seed type
-Where the tobacco is grown
-How the tobacco is grown
"Connecticut"
likely means it is tobacco grown in CT, with a seed that was originally brought over from Cuba or Sumatra. But you also have those same seeds grown in Ecuador and you get things like the
E.P. Carrillo New Wave Connecticut which has a wrapped made with tobacco grown in Ecuador with seeds originally from CT. This is quite a common story as Ecuador has boomed as a tobacco producing country. A cigar I really like (before they recently changed the blend
) is the Oliva Serie V Melanio Maduro which has Ecuadorian Sumatra wrapper with a Nicaraguan binder and filler.
"Shade" as you referenced with regard to one stick means that the tobacco is grown under some type of cover that filters out some (but obviously not all) of the harsh rays of the sun. Typically directly sun grown tobacco is stronger, has bolder flavors and a higher nicotine content but shade grown is in very high demand because it makes great looking, mild sticks that are very accessible to new cigar smokers or people smoking cigarillos.
Obviously as you continue into this hobby you will learn what you like or dont like in a cigar and how to pick out and differentiate more flavors. So when starting friends off I like to ask about some of the things that are easier to pull out. Some words common in describing cigars that I flavors I find people can pick up on quickly are "spiciness" "hay" and "nuttiness." In general you will find that sticks with dark wrappers like the Drew Estate Liga Privada or many RoMa Craft cigars are "spicier" I would recommend giving one of these a try to understand that profile. In general you find a lot of "barnyard," "hay," or "grassiness" in Cuban cigars, but I find these are also very present in Plasencia's offerings. Most of Arturo Fuente and Padron's lines have a nutty flavor and I often suggest the Arturo Fuente Gran Reserve 8-5-8 as one of the best intro cigars. My top recommendation is to pick the 858 up in a few different wrappers (claro, maduro, and natural are all pretty easy to find). Its a good intro stick, the claro is quite mild, the nuttiness and spice (cinnamon, etc) flavors are easy to pick out and its a good way to compare various wrappers.