Technical limitations similar to the ones which developers need to respect while crawling sites?
And can automated scripts be written with the limitations in mind? What are the possible bottlenecks for such operations?
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I recently found this one out, but there is no checksum - so enter carefully or use a namereg according to Vitalik:
You're not meant to use ether addresses; you're meant to use the namereg and equivalents of things like bip70.
Taylor also mentioned it may be added into a version of Ethereum post homestead.
I think everyone wants checksums and understands the benefits, but delivering a stable network protocol upgrade is of chief importance right now and has been since the beginning. Additional functionality in the clients themselves will hopefully follow soon after the Homestead hard-fork. :)