I too would love to look into this. I spent a bit of time researching Kaliedoscope and Plex, It seems like a lot of work to initially setup, but once done having the ability to download torrents automatically or with a text sounds amazing.

The harder part would be convincing my girlfriend and roommate to ditch cable... We have the option to get gigabit internet but I was outvoted on the switch. Gotta fork over money to Comcast because they don't mind the ads.

A NAS, something like a Synology DS218+, is fairly easy to setup. I'm not a sysadmin or anything like that, though I do have some experience with Linux (2000-2005). My main OS these days is MacOS. I wouldn't want to have my 70 year old father try to set it up, but if you're on Hacker News you probably will cope with it ok.

It's my opinion that it's more time-consuming and tricky to rip/re-encode everything. I use MakeMKV and a few extra apps to rip/convert subtitles. Handbrake is, seemingly, what everyone uses to convert to MP4/MKV or whatever... and it takes a fair bit of patience to find the sweet spot of quality, size, and compatibility.

I started ripping/converting DVDs and BluRays last year around this time and I'm still on it. Some of that is due to the fact that I've had to go back and re-rip stuff and some of that is due to the fact that the machine I'm using for conversion is about 10 years old. A BR film takes about a day to a day and a half to encode.