I think the biggest hurdle is that he is in no way techy. I'm lucky he charges his phone. He just recently figured out email and Netflix within the past year, and aside from Craigslist, that's all he does online. I rotate him through my eGos and Spinners, he can't put one on a charger when he gets home, he waits until it's dead and tells me. I have an Evod designated for "his juice" now, that I have to check the level on once in a while. I left the bottle out, and on my way home get a frantic call from him saying he thinks he broke "the thingy." He tried filling it without taking the base off. By now you'd think he'd have seen me fill things enough to know the base screws off. But no.
So, basically unless I do all this for him, he's doomed. We shall see.
I have now converted (or in some cases, mostly converted) seven people from smoking to vaping. Here is how they've done so far... I promise this list will make you feel better.
My mother (age 60, vaping about 2 months): "My thingie is empty."
Me: "Bring it here, I'll fill it... you could do this, you know, it's not hard."
Mom: "I know, but it's technical. Did you order me some more batteries without the button? Those ones with the button are *stupid*."
Me: "I will on payday. What flavor do you want?"
Mom: "That one you were vaping three days ago."
Me:..... which one?
Mom: The one that smelled really good.
Me:.... that doesn't help me. Here, sniff the bottles."
(end scene)
My father (age 60, vaping 2 weeks): "Hey, that 100% VG stuff is good. How do you charge the battery again?"
Me: "You screw it into the charger, Dad."
Dad: "What charger?"
Me: "The one I gave you."
Dad: "Oh! Thanks. I've been using (stepmom's) battery all week cause I couldn't find a charger that fit."
Me: "Uh... dad?.... you realize I gave you guys functionally identical batteries with functionally identical chargers, right?"
Dad: "Oh....

.... sorry about that."
Me: No problem.
Dad: You'll get old too one day.
Me: I can only hope, yes.
(end scene - I would like to add that this is the man who taught me how to program things in BASIC, amongst his many other accomplishments.)
My best friend whom I've known since I was 12 (age 33, vaping for ~3 weeks): Hey, this vaping thing you're doing - I've got some batteries and some juice, but the juice I've got is a no go for me. Can you hook me up?
Me: Sure. Here's some clearos, and some more juice. Want to try my MVP2?
Him: "Holy

! That

hits like a train! I like! Where can I get one?!
(A week later)
Him: The guys at work are now calling my office "G's Bakery." I told them not to smart off to the boss."
My stepmom (age 55, vaping for ~2 weeks): Show me how to do this.
Me: Sure.
Stepmom: Okay, I think I got it. Show me one more time.
Me: As many times as you need.
(5 minutes later)
Stepmom: This is kind of awesome. Do they make (certain plant flavors)?
Me:.... Er... yes, actually.
Stepmom: Really? I'm about to relive my youth!
My grandfather (age 80, vaping ~2 weeks): So the liquid goes in here? Pass me that coffee. *puff, nose exhale, long draw, satisfied exhale with a *huge* cloud of vapor* Yeah, that's really nice.
Me:..... on your first try, too.
Grandpa: I've learned a few things.
Friend's daughter (27, vaping ~ 1 week): I can't get the liquid in the thing, it just dripped all over the table.
Me: Show me how you filled it.... that's the bottom. Pull the mouthpiece off, remember, just like I had you do the first time.... *there* you go.
Friend's son (30, vaping ~ 1 week): Man, I'm liking this vaping thing, but I need a little more *power* now, you know?
Me: Like this? *sticking a drip tip cover on the MVP and passing it over*
Friend's son:

! Yeah! Where'd you get that?... and can I get a plain one or do they all say "police public call box" or whatever?
Me: You can get them here, and they come "plain."
In sum, everyone is different... but man, it's fun to convert people.