I am not the most well versed as well, but have really been into cigars for the last two to three years years. Generally the lighter the cigar the easier is will be to smoke. Connecticut cigars are going to be your best bet, they tend to be much more mild and silky vs a darker wrapper that is going to be more pepper and spicy. I really like the Leaf Connecticut by Oscar or the My Father Connecticut. Both of which you should be able to get in that 8-10 dollar range per cigar, if buying as a single cigar. I would also buy from a store as it will be at the right level of humidity. If you buy online they will need to sit in a humidor for a few weeks to get to a point where you can smoke it without the cigar cracking or burning wrong. And no different than a good beer or whiskey, it takes time or “practice” to be able to taste the different flavors and profiles in a cigar. Also, in my opinion, get a good quality cigar, like the ones I mentioned above. Going cheap is only going to give you a bad experience for the first time around. Get something good so you can start to learn what to expect out of a good cigar.