Custom Video Players
Jamroom Developers
There is the 'Playlist Ads' module that allows you to inject adverts into audio playlists.
https://www.jamroom.net/the-jamroom-network/networkmarket/64/playlist-ads
The limitation with Playlists is the player, not the Playlist module. It could be customized to build a list of videos, then insert adverts into them.
Or you could customize the video player.
Each skin has an include.php file in it. In that it specifies the player to use, eg in the jrSoloPro skin's _init() function
jrCore_register_module_feature('jrCore', 'media_player_skin', 'jrSoloPro', 'jrVideo', 'jrSoloPro_video_player');
That will then use the
/skins/jrSoloPro/jrSoloPro_video_player.tpl
for the videos. You can do the same and setup whatever player you like with it. We currently use the jplayer because its license ( MIT ) is compatible with our license ( MPL ).
On your site you don't need to worry about licenses because you're not distributing it so you can use whatever you like.