Cannot get Plex to stream from my server

I’m reposting this here because its been about a month of no replies on the Reddit.

Have you checked the Plex knowledge base and searched on the subreddit and Google: Yes.
Server version: 1.3.3.3148
OS: Windows Server 2012 R2
Clients, w/ versions, if applicable: TiVo, web
What you did? Fresh install of Plex onto the server. Tried to play ANY videos through TiVo, and also several videos through Web.
What happened? Every play on TiVo either froze or errored. Through the web client, most videos failed with the error “There was a problem playing this item.”
What you expected? The video to play.
What are your (relevant) settings? Not sure what settings might be relevant. This is literally a vanilla fresh install. There’s plenty of free disk space.
Link to logs (optional but recommended): https://gist.github.com/bytenik/86cac4f37362758be9ef903acddd6b02

Welcome to the forums. FYI - Plex does not have an official page on Reddit.

Your log shows you trying to direct play an FLV file in Chrome. Chrome started recently to disable the internal flash player, which could cause the file to not play. There should be a setting in Settings \ Web \ Player to use the HTML5 player. Please make sure this is enabled, which will enable Plex’s player. This can’t play FLV directly but should get your server to transcode it to a playable format.

As far as your Tivo, I don’t seem to see it in the logs. Can you try playing something from it and provide me a new log?