Connecting to relatives

A general advice-seeking post:

I have a Grand-dad (Pop) who's a really neat guy. It's galled me for years how I've been so far away from him and haven't been able to be close. Well, we lost Grandma recently, and I'm damned if I'm going to lose contact w/ Pop too, if I can at all help it. My brother in DC recently set him up with web-mail, and I've sent one or two missives to little or no avail. It largely seems like he just minimally responds to the email like checking off a box on a to-do list. I'd like to assume that this's just because to his generation email isn't a native medium like it is to us, especially when it works through the TV-set, which's a horrid interface. Irrespective of that, I feel like I'm totally failing to engage him, even though I'm trying to connect in subject areas personally relevent to him too (aka not talking about the new programming language that's taking up so much of my time). Any advice?