Thanks everyone, I feel much better about moving forward. I'm leaning towards Proxmox at this point because I could still run Windows as a VM while playing around and setting up a new drive pool. I'd like a setup that I can gradually upgrade because I don't often have a full day to dedicate to these matters.
MergerFS still seems like a good fit for my media pool, simply only to solve an issue where one media type is filling a whole drive as another sits at 50% capacity. I've lost this data before and it was easy to recover by way of my preferred backup method (private torrent tracker with paid freeleech). A parity drive with SnapRaid might be a nice stop gap. I don't think I feel confident enough with ZFS to potentially sacrifice uptime.
My dockers and server databases, however, are on a separate SSD that could benefit from ZFS. These files are backed up regularly so I can recover easily and I'd like as many failsafes as possible to protect myself. Having my Radarr database was indispensable when I lost a media drive a few weeks ago.