Hi Alex,
Signing emails from hostmaster@ripe.net, lir-help@ripe.net, new-lir@ripe.net and enum@ripe.net is one of the first pieces that we need to remove in order to phase out all the legacy software. While we realise that it is a best practice to sign such emails and are aware of the value it offers, we are planning to discontinue email signing from just these addresses starting 1 January 2014. It will allow us to phase out a part of our infrastructure that makes future migration a lot easier, while saving cost in the mean time.
Bad idea. Come on, it can't be that difficult or expensive to add a digital signature to an e-mail. There are command line tools that can do that in a single line, and there is Python code that can do it in ±10! I don't know what software and language you are using, but if adding a PGP signature to outgoing messages is as hard as you describe then you're doing something horribly wrong... - Sander