The smart playlist in iTunes is a bit smarter than plexamp. One thing that is really noticeably missing is the “Limit To”, really needs to add an “at random”. I’ve seen some prior forum entries explaining how you could do this, could not see them actually doing anything useful. but even if they did, they are obtuse at best. I want to be able to select ## tracks at Random based on what I’ve selected, regardless of how the Library is listed.
Thanks for asking for this feature. I have started to create smart playlist using the obscure random feature you mentioned and was going to ask for this useful feature. I second this request.
Pro tip: If you create a smart playlist without sort order and download X hours, you’re essentially doing exactly that, as it will take a random sampling of the playlist. If you’re not downloading, then not exactly sure how the limiting is super useful but maybe I’m missing some scenario?
For me, not focused on downloading, but attempting as much as possible to create the “radio” feature of Plex using a more specific and tuned set of tracks. That is what I like about random feature. Certainly, I would really, really like the ability to build up radio sets using any criteria. For example, I can do 1960s radio, but the music style in 1962 and 1969 are quite different. How about the ability to do radio for 1961-1965. And if you give me that, why stop there. Let me build a radio using genre and album date and style and whatever. That would be cool!
Slight hijack, but how do you creat a smart playlist without a sort order? All my smart playlists are sorted by “Album Artist” by default 
There is a way to specify sort=random. Find the sort= column in url and change value (artist name) to random. Not a very public trick, and I honestly forget where I read it. That is why I request and explicit option in smart list creation screen.
Yes, that is the great tip. Now, all we ask is that the Plex engineers add a “Random” check box in the filter dialog so I don’t have to go to the URL and physically add the random parameter. Just a cleaner interface.
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EXACTLY… I shouldn’t have to be this smart to create a smart playlist! 
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