I heard that Koryo Tours (the biggest travel agency catering to westerner tourist wanting to see NK) does give "special tours" to those people paying extra $$$. A few rollercoaster enthusiasts asked for a special tour of North Korea's communist-style amusement park, and they got what they asked for. It's surprising!
So, if you have the $$ (unusually large amount) and you're not an American (since that's probably illegal), you could ask Koryo and see what they can do for you... They already have a dropzone (see davelepka's photos above).
I saw a bunch of NK photos on Flickr, and it's rather eerie, interesting. Controversial mind you, but very interesting to watch the evolution over the last ten years.
[Background info about ongoing NK developments, interesting to tourist POV. Not starting anything political -- just some interesting background info useful to tourist POV] They are one of the world's most tightly controlled societies. But from the changes in the photos on Flickr, they seem to be on some very early verge of something new, much like China's changes starting in 1980's. Tourists from the Western economies are mentioning that NK has changed a lot in the last 10 years. Though they finally have their 3G mobile phone explosion (94 percent of NK's 24M population now has 3G signal, over 1M subscribers, growing fast), and the mobile phones are finally even spreading to the rural NK poor because NK's countryside now has good 3G reception, and generally slowly starting to discover the 'outside' world (NK citizens texting in their country-only texting network, about secret meetings to meet to watch bootleg DVD's of western TV shows. Very few have access to DVD players, so DVD-watching is often a very large social affair in North Korea) and discovering what Westerner lifestyles are like, despite tight filtering -- to government chagrin -- only recently. Leaks are starting to slowly occur. In fact, just about barely enough computers have now shown up in NK schools/instutions, that a few NK citizens are meeting at them to do file sharing, by sneaker-netting files between electronics devices (i.e. cellphones/MP3 players), sharing foreign audio/video media between intensely curious NK citizens, and easily-hidden microSD cards readable by now-suddenly-available cellphones. Interesting developments. Although scary-tight society, NK seems on the cusp of being 'enlightened'. Anyway, meanwhile -- tourists are also being allowed to do more than they used to, and with fewer guides/minders than in the past, apparently -- I suspect it won't be long before a rich tourist is allowed to skydive in NK (after some payoff to an NK-approved tourist agency) probably within 5 years -- at least as tandem -- from the patterns I'm seeing in Flickr tourist photography of NK's slow changes and what they're starting to let tourists do, and they do already have a dropzone. People fascinated by Perestroika developments of the 1980's, should start popping their popcorn now.
Since NK has at least one dropzone and at least one tandem rig, what this means for the OP, given a neutral/enthusiac tourist, it's probably realistically expect that said person to recreationally skydive in NK well before the end of this decade if they begin the process now (if one tried very hard to make it happen). I'd imagine one would do it in steps -- visit first to their 'extreme sports' stuff like amusement parks and whatever they've already let tourists do. This gives them the opportunity to do some "networking" about seeing what the leads are for the not-yet-tourist-allowed activity, and establishes a tourist relationship that contributes to state coffers. Then during next visit, successfully convince an agency to arrange a tandem. Then actually visiting for a tandem and doing the jump, also showing them their own skydiving license. And then on their third visit to NK, revisiting another month or two, actually do their solo skydive (to give time for the bureaucracy to grinds along to allow it to happen) -- Might not let them bring your rig, but might "rent" them one for the right price. Given a determinedly enthusiac visitor with lots of money and lots of patience, obviously. At least, so the pattern goes in how NK travel agencies "seem" to work these days for unusual tourist requests... All theoretical, of course, given sufficient money offered. If you're lucky, one might be able to pull this off in just two visits, rather than three or four. Maybe not. But it seems unusual requests are starting to be granted to rich tourists nowadays, as they all know NK's famous thirst for funds. And their photos/youtubes are always interesting. Not condoning it, and USA prefers you not send tourism dollars to NK, and we all hear about the controversies. But one can be fascinated by new photography/videos (and NK being curious/witnessing outside tourists tends to be a good thing in slow enlightment process).
NOTE: Easier challenge first (and rehearsal) is to skydive in China first. Only recently, it's become possible for tourists to skydive in China. (Beijing Shahe Airport, at least) Very pricey, I heard.
Watching with popcorn, though, from a distance. Student of history. (Merely vacationing in NK is an extreme sport!) It's all interesting to watch, no matter the controversies.
(This post was edited by mdrejhon on Jun 26, 2012, 12:06 AM)