IMHO you're going in the wrong direction. Don't go bigger and more complicated. Keep it simple and closer to the smoking they're used to. Buy them each an Njoy Bold and see what they think. If they like it get them both Erolls. They've smoked for a whole lot of years. That's what they're used to. Vaping is a pretty weird feeling to get used to and doesn't substitute for the feel of a cigalike. I still use an Eroll along with my other setups. I use it when I have the urge to smokell like when I do things I always smoked with... going for a walk, sitting outside, talking on the phone... old habits are hard to break. I need the feel of a smoke then still.
This. I was going to suggest something similar but patkin beat me to it. I am one of the few on here who love my cigalikes. Njoy is supposed to be one of the most similar to analogs, there is another EHookah/Ecig company that makes disposables with soft tip that is also supposed to be very realistic called Rejuve, might check into it.
I love my little cig a likes, the key to long term use is to have plenty of batteries, I like my shortys, they do not last as long but they are teensy and so lightweight. I am vaping Buttery Nipple right now off a V2 shorty. I use both prefilled and blank cartridges, I refill my prefilleds even, to get a little more money out of them, but honestly, you don't have to. You can just open the pack, screw on a new prefilled, boom, good to go. Aside from going through disposables, I cannot think of anything easier.
I know most vapers on here do not see the point in cig a likes but it seems the majority who start vaping on their own go through a cigalike transition. Those of you "helping" friends and family get started and going to typically bipass that step, it seems totally logical to you, but maybe some folks need that transitional step to get used to vaping. Perhaps starting them off with more advanced equipment is just too much of a change all at once.