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organizing by area

I find mail-to-jail.com highly valuable. I think that if you wanted to set up subdomains like Mr. Helwig suggested, that you could assign administration of those subdomains to an interested party.

For instance, those wanting to head up an subdomain for Bradly Manning could administer the mail for that subdomain. Likewise, is someone wanted to handle mail for a particular prison that was not in an area you are interested in, say, MCI - Cedar Junction (Massachusetts Maximum Security Prison), then you could assign rights for mail directed to those areas.

As for the fun-packs, I love this idea. I was thinking about providing a service like this for prisoners through my website as well. I've been crunched for time, and if you are working on it, I won't duplicate your effort. Maybe we can work in conjuction.

rambling

Subdomains, like Porc411 - maybe for each state, maybe per person jailed.
Make placeholders with a ChipIn for each subdomain until enough has been raised.
Ask for subscriptions, and activate subdomains when you get enough subscriptions.
On each submission form, be sure to have a donation beg, specifically ask for at least as much as you figure it costs in time and materials.
The fun-pack idea is awesome.