For listening to pirates, it would need sideband, or as you say, some tricky situations with AM signals. My cheap shortwave radios just use a BFO at the IF (intermediate frequency) to inject a carrier, simple and works well enough once you get it tuned in. I've also used the BFO to pick up AM stations too, parking it on top of the AM signal's carrier to push out some noise to hear the station better.
I notice a lot of the buzz around the radio is about the DRM digital reception capability, and I wonder if that's to present an appealing, high tech side to the radio, and/or a push from the players promoting DRM, to get cheaper digital receivers into the marketplace. The press surrounding the Titus and those guys on the recording were so excited about its DRM mode, way more than listeners seem to be at street level.
Maybe the shortwave bands will be good territory for digital signals one day, even quality local services on some bands, since we're running out of space on FM, so a programmable receiver like that is good. Right now though, I'd want great regular analog features like real SSB as you mentioned, variable bandwidth, noise blanker, synchronous tuning, with all settings accessible to the 'knob turner', plus just an auto mode for easy use
Boomer