Cigar smoking is not for everyone. It takes time to acquire the taste.
I started smoking Dutchmasters and another brand I can't remember while still in high school. Cheap machine rolled cigars are not the same as good, hand rolled sticks.
My first hand rolled cigar was a Carlos Toraño Reserva Selecta I bought during my Junior year of college in 2004. It was a very different experience. It was so much smoother than the gas station Dutch's. If you took the time to experience the flavors, the complexity, you found great pleasure. It's line the difference between cheap beer and craft. Or cheap whiskey and single malt Scotch. Each batch is unique.
If you truly want to try to understand why people love cigars, I would challenge you to do sn experiment. Get a cheap cigar like a Dutch (stay away from Swisher Sweets or infused or flavored cigars), and smoke it. Then get a good, hands rolled cigar, like a Toraño Exodus 1959 or 1916 Cameroon, or an Arturo Fuente, and smoke it. Don't do anything else while smoking them. Just concentrate on what you taste, smell, experience. See if you can find the difference.
Another avenue to try, would be an Acid Kuba Kuba. These are infused cigars from Drew Estate. There is a particular flavor that is very enjoyable with these. They are what I offer people who want to smoke a cigar, but are not really cigar smokers.
One word of caution, when just trying a cigar, I would avoid maduros (the reality dark wrappers). In my experience, they can screw with people's heads if they are not used to cigars. Also, I would not start a newbie on anything from Gurkha cigars.
"A man will give you a cigarette, offer you a cigar..."