Okay, let's get at least a concept rolling. Should this calendar look like a Dieux du Stade type thing, glamour calendar, men at home, out in nature?
Give us some ideas, we'll decide on a look and start culling applicants & organizing photographers.
Who owns LPSG & how do we contact them for permission?
The cost would be substantial and you'd need to have proof of age meaning models would have to divulge their true names to LPSG and the calendar publisher who would then keep their ID data on record. You would also need written permission from the models in question allowing their likeness to be used in print publication.
Getting professional quality pictures is not easy. Nude photography that's of exceptional quality requires substantial investment in talent and equipment. Otherwise it just looks like porn. Now some guys might be fantastic photographers, capable of taking photos that will look super professional on 93.5 sq. inch hi-quality glossy stock, but assuming they're not, you'd need a professional nude model photographer to travel to the models or have the models travel to the photographer. The entire project would have to be overseen by an experienced art director. Then there would be the cost of printing, binding, and distribution.
Calendars are largely impulse buy items. People buy them as gifts when they can't think of anything better or group them in with other gifts. You can buy calendars on Amazon and such, but brick and mortar retail would bring the best returns. That is if you could find a retailer that would carry a nude calendar. Many national chain retailers have a prohibition on the sales of media containing, "nudity with an intent to arouse the libido," OR require that items containing erotic nudity be kept behind the counter -- not a good situation for an item that is largely an impulse/quick decision buy. LPSG could also find itself the target of unwanted publicity should the calendar contain content offensive to local standards of decency. A flaccid penis can usually be classified as art. An erect penis is a far more difficult sell (just ask the ghost of Robert Mapplethorpe) and many places in some jurisdictions would interpret the depiction of an erect penis as obscene.
There is merit to the idea but of course the ultimate question is what charitable organization would take donations from an adult sex website? Perhaps there's a rest home or health care fund for down-and-out porn actors, but otherwise I literally cannot think of an organization that would readily accept a check from LPSG simply because of the nature of its content. For the charitable donation to be of value to LPSG, the charity needs to publicly acceptable. I don't think LPSG nor potential purchasers of the calendar would like their funds to go to a Future Seal Clubbers of Norway youth group even if they would take the funds.
I like the idea with the caveat that given all the considerations, the calendar would likely have to be professionally produced and marketed. Done propertly, targeted to the right consumers, it could bring the site a great deal of
good publicity. Ultimately it's up to Rob as LPSG is his homonculus.