I started smoking due to a very weird and restrictive upbringing. I started smoking late, at 18, but ever since I can remember I always had an oral fixation due to the ridiculous amount of stress and anxiety I grew up from birth. I was the kid always chewing on a lollipop stick or destroying his fingers by biting his nails. I was actually diagnosed with stress and anxiety disorders, chronic depression and social phobia in my mid teens. I never got into smoking because I was taught that basically any substance other than food, water and liquor in moderation would land me in hell. Anyways, I finally decided to start smoking artisan cigarillos when I was with a friend who was buying some for himself. I asked him how to inhale and he said just straight lung hit, and that's how I smoked my entire life, straight and full lung hits. Smoking was a big distraction for me from all those issues I was having, and allowed me to feel a bit more normal and in control of myself, most likely a placebo effect since I mostly would go off and smoke at the beach where no one could see me and just think.
I quit smoking when I met my girlfriend at 21. Her mother had recently undergone chemotherapy for breast cancer and they had both quit smoking when they found out. I started smoking less and less the more I spent time with her and eventually they tasted too bad to want to pick one up. Still, all those anxieties were always there and I would still think of having a cigarette even though I never picked one up. I think my first e-cig was some crappy little ciggalike that was quite bad. Like described above, sucking through a straw for very little vapor and no satisfaction. I eventually quit that and some time after that picked up an ego twist and some clearos, which were better but I lost interest relatively quickly as I couldn't do my full lung inhales. It wasn't until I got an Atlantis and CF mod, along with a dripper that I started feeling some satisfaction. My mind would go from anxiety more towards vaping, and once I got a mech mod and finally my 150w mod and slowly went from 0 nic to 3 nic that I found full satisfaction.
I'm automatically a cloud chaser as I have big lungs and good lung capacity, but I feel like I always was. I loved watching the smoke rise when I smoked and blowing smoke rings, all things that gave me a distraction from my screwed up brain. I no longer thing of smoking anything other than those vanilla cigarillos that I started out with, as vaping is even better at giving me those things I liked from smoking.
Sorry for the long ramble. I've read many people asking questions about why people start vaping, and how some don't see why a smoker would need to sub-ohm cloud chase, and I couldn't think of any other way to respond here without all of that lol. I can talk quite a bit as you can see.
Oh, and as to the question on the title, I'm actually going through this right now. My friend still smokes and isn't satisfied by ecigs, likes the heat and yadda yadda, so I'm trying to give him a few things to look at that I feel will give him that satisfaction. So basically, I would ask a bunch of questions about their smoking habit; how much and how you smoke and what you like about it specifically and go from there.