PowerPress does, in the form of "Podcast Channels". Enable the option "Podcast Channels", add the number of channels you need (e.g. 5 audio, 2 video if you have posts with 5 audio files and 2 videos). Then go to PowerPress > Tools > PodPress Import and import your old podpress data to the appropriate channels. You will also see new podcast episode entry boxes in your post edit screen for each channel you add.
PodPress back in 2006 added multiple media files per posts without any real research on the topic. Even though you can do it to a page, it messes up the feed big time because most all podcast services/apps such as iTunes only grab one media file per post, sometimes only the first media file listed, sometimes only the last. No player lists options for the user to select from to play.
This is the difference of doing things "the right way" vs "doing them because you can". You can drive a car the wrong way down the street but it doesn't make it right.
PowerPress solves this the right way by mapping each media file to a unique feed (Podcast Channel), so you can have a PDF podcast feed, a video podcast feed, an audio "ogg" feed, and a regular podcast mp3 feed for example.