James has 300 DVDs that he'd like to put on a media server and watch using Amazon Alexa to launch them. Rich says that the first thing James would need to do is "rip" them to a hard drive. He can use a combination of HandBrake and VLC Media Client to get them into digital files. Then he can put them on a network attached storage device.
Rich likes Synology. James can just connect a few hard drives to his network. Having them set in a RAID 5 configuration would be best. Then he'll want software that will interface with Alexa and enable it to play, like Plex. The basic functions are free. He can just Install Plex on the Synology and then connect Alexa to it, and it should all work the way James needs it. But it will take a while to get those movies ready.