Some of the links on this forum allow SMF, at no cost to you, to earn a small commission when you click through and make a purchase. Let me know if you have any questions about this.
That sounds like some sound advice, I don't have any experience on either but I would think it would be a safe bet that either of those two options would probably come with less frustrations / learning curve.
I'd suggest you go not with a $300 smoker, but with something under $50. Get him a cheapie gas or electric with a promise to upgrade if he likes the idea. That way, he can get his feet wet so to speak, then make his decision on which way he wants to go.
I don't one, but if you go electric I also nominate the Masterbuilt at SAM'S as well. If he has expressed interest in charcoal a Weber Smoky Mountain 18'5" would be my suggestion in your price range. I have one and love it, once you get it figured out (which shoudn't take too long) it very easy to run. My only complaint is that I don't have the 22", but it is well over $300.
The down side to electric is that you will also have to purchase some sort of smoke generater (creates the smoke). The propane smoker is good to go just add chips to the chip pan. as far a sclean up, you only want to clean the racks and the bottom if any liquids happen to miss the drip pan. hope this helps, and trust ALL OF US, he will be addicted.