Longer cigars usually burn cooler and have a smoother more mild taste, but that's not a rule.
Starting out with a Churchill is probably a good bet.
Look for a wrapper that's not too dark, a light tan is usually mild.
Most cigars in the $5-$10 range are average to good in flavor.
Yeah. I'd read up on cutting and lighting.
I usually like to cut a full cut so the most smoke makes it through, but as close to the tip as possible so the wrapper doesn't unravel.
Then I usually put it in my mouth and get it wet, that helps it keep from coming undone if you accidentally cut it a little off.
Then I only use wood matches, I light one and let it sit for a second until the head is burnt, then I roll the foot(end) of the cigar around as I hold the foot to the flame. I hold it at an angle.
Then once the outside of the foot is lit, I hold up a new match about a quarter to a half inch from the foot and with it in my mouth, I start to suck the air through it while turning it to get it lit. If the end flares up, I make sure to turn it more until the foot is lit.
Then, take some long slow puffs to get it lit nice, and let it sit for 30s-1m to let it cool down.
Then I smoke it. Making sure I keep turning it so it burns evenly. Most avg real cigars burn even, but sometimes you'll get one that doesn't, especially if you hold it in any way other than level. I smoke it slow, to keep it cool, usually taking a quick puff to make sure it's burning well followed by a long slow puff to get some smoke.
Then I enjoy until I can only hold it with two fingertips.
-A torch lighter is an acceptable substitute for wood matches, especially if it's windy and you're outside.
-Longer is usually better, at least in my experience, though bigger ring gauge doesn't necessarily mean better.
-Torpedo cigars are easy to cut, maybe a good one to start with.
-Candela(green) wrapped cigars are very smooth and mild, though the flavor is a little unique, so starting with a tan one is probably best.
-Keep it burning cool for the best flavor.
-To keep it from going out, puff it quick a couple times if it's dying instead of relighting after it goes out.
A review of the 5 star rated cigars in the cigar database would be a good start.