To see anything like that in the PRV for a MIDI drum track you will need to use a drum map. You have to set the output of the MIDI track to the drum map you want to use, and make sure the drum map is visible in the PRV. I've been fooling around with the free SSD 5.5 plugin and looked around for a drum map for it but couldn't find one. I don't have much experience with making drum maps so I thought it I'd give it a shot. I made an SSD 5.5 drum map for Cakewalk, including the notes where no sample was loaded, using the note map in the SSD 5.5 synth with the Deluxe 2 Free Hugo preset. It seems to work okay in CbBL and Sonar if you want to check it out. Any corrections, suggestions, or complaints are always welcome. Put the attached file with the rest of Cakewalk's drum maps and it should show up in the list.
As far as making the notes show as diamonds with no duration, I wish I knew how to do that. I usually use the Event Inspector to change all the durations to 84 and seems to work pretty good for me.
The generic Steinberg low-latency driver has been known to cause problems with Cakewalk's ASIO function. Here is what I would do if I were you. Completely uninstall the Steinberg audio driver (I would use Revo Uninstaller) and install the Yamaha Steinberg audio driver. The driver is part of the Tools package, or can be downloaded and installed separately from the Steinberg website.
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Chaps's post in Is there a simple way to add custom note names in the PRV. was marked as the answer