The Chrome extension keeps the player always on top and easily accessible. You can resize the window that pops up to only show the player controls. Log into your Plex Web experience and right click on a link (Music for example) and select the new option "Open link in Panel". Quickest way to make that happen is to type "chrome://flags/#enable-panels" in your address bar of Chrome and simple click "enable".
Once installed you will need to configure Chrome to allow panels.
In chrome app store search for the "Picture in Picture Viewer" by a developer called Chongz. Pre-requisites: Chrome Browser, Access to your Plex Web, Ability to Install Extension in your Chome browser. Note - This is not a custom application, it leverages existing software and the plex web portal. I mashed up a solution that I have been using for a few days now and figured I would pass it along to the community as my previous searches yielded no results. One thing that I wanted was a player applet or dock that would provide quick access to the media and controls to the bottom of my screen, always on top. I access my Plex Web at work to enjoy playing my music.
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