I'm looking for a free program that would allow me to convert DVDs & VHS videos and then stream on my tv. I would like to be able to run this software on a VM on a home ESXi server. I am new to these technology's.
Hmm.. that's why I said "look into"I'm not certain that I'd recommend H265 just yet as many media players don't support this format natively and, therefore, Plex will likely have to transcode each stream. While it's definitely the future, I'd wait a couple of years and use x264 in mkv or mp4 containers for now. The file sizes will be bigger (4-5gb for decent 1080p with 6 channel audio ~2 hour long movie) but they'll be playable on far more devices.
Handbrake + Plex. Handbrake can be used from the commandline and so you can setup your own full/semi automated workflows.I use handbrake on my desktop to rip/convert DVDs and a VM running Plex to serve everything up to my TiVo that runs a Plex app.