TrueNAS might be a good middle ground then. Haven’t used it myself but I’ve heard a lot of good stuff about it (and it’s predecessor).

It really comes down to personal preference. A pure Linux distribution for example is certainly more flexible and will absolutely do everything and more that TrueNAS does. But a nice gui where everything just works and does exactly what you need sounds x100 times better than spending a whole weekend trying to fix something that you borked by accident. And if you want to learn how things work under the hood later on, you can do it at your own pace. At a certain point those terminal commands will stop being esoteric and start making sense.

If you have some old hardware just lying around, then install it and try it out. Just dip your toes and evaluate for a few days/weeks.

Also - after some quick googling. Mounting your windows disks shouldn’t be a problem. So no need for some temporary/intermediate storage unless you want another backup.

I also have a Pi with HomeAssistant that I’d like to migrate

I would (read: does) keep it that way. When your server inevitably goes belly up because of a misconfigured firewall or whatever you’ll thank yourself when the lights still turn on and your robot vacuum keeps going. No stress to fix things. And when your SD card eventually dies you just pop in the backup card you have lying around.

I am wanting to do this in the most efficient and economical way but I’m not sure what the best path to choose is.

What’s wrong with keeping your old hardware? Spend some money on a silent quality case, a few quiet fans, a suitable power supply and some disks. The rest can be bought used if you need it, dirt cheap. Find a somewhat new Supermicro motherboard with a mounted CPU on eBay for a few bucks and be done with it. It doesn’t sound like you need a monster machine. Some overhead is always nice, sure, but you can always upgrade in the future.

Migrating data is a PITA no matter what so can’t help you there.

As for the OS. “Not Windows” is probably a bit intimidating at first but you seem to be pretty technical so it isn’t really an issue as long as you can read and process information. Do some reading on Debian or FreeBSD (or both). BSD isn’t Linux but if you’re not familiar with either one it doesn’t really matter. Just a matter of taste. Try them in VirtualBox and see for yourself how you feel.

And let us know when you buy your first rack. It’s just a matter of time.

iOS used to be an absolute pain in the ass. Had to scratch my head for several days a few years ago. I believe it was iOS 15. Forcing SSL and self-signed certs with some odd flags finally did it but it was not straightforward. Good luck reading logs on an iPad. Unfortunately I don’t remember any specifics.

Other than that I’ve had zero issues with Baikal for the last couple of years. Roughly 15 devices (iOS, Android, Windows, Linux), and 5 users each with multiple calendars, tasks, contacts, notes etc. and everything just works. DAVx is excellent if you use Android as CalDAV isn’t natively supported for some reason.

But I get your point. CalDAV as a standard has always felt a bit… Janky? It never left the early 2000s. So setting up a CalDAV server in 2024 isn’t particularly difficult but everyone wants their own implementation. And your server/client combo probably require you to find some obscure forum post from 2009 and reading the man pages several times before you find that one specific fucking legacy parameter in some config file that has to be set.

You could always set up your own Exchange server though if you’re a true masochist.

I guess it depends on the use case. If you prioritize network and zfs performance, sure. There’s a reason why the Netflix CDN or your router runs some BSD derivate.

I’d argue that the jails are a feature that hasn’t been replicated. Each jail is a container and can be set up as an isolated environment with its own filesystem, network stack, set of user accounts etc. I know there are a few similar solutions on linux but nothing that is so deeply integrated.

Yes, of course. I believe it was a NetBSD developer who initially wrote it.

For a server - it’s fantastic if you’re a reasonable adult and if you don’t have a compulsive need to install every shiny new “app” you find on the internet. Terrible if you hate reading any kind of documentation. Terrible if you already decided that some of its core concepts are stupid and try to force stuff in order to mimic your favorite Linux dist.

Takes some knowledge and planning to set everything up properly but when it works, it works forever.

ZFS works as intended. I hear that it’s miles better these days though in Linux.

Jails will make your life so much easier.

If the software isn’t available in the ports tree you don’t need it. You may want it but you really don’t need it (bro just download my Docker image, I wrote a webserver in rust bro I promise it’s super stable and it’s never been done before bro). Enable Linux binary compatibility or fire up a virtual machine with a tiny dist if you’re a masochist.

I personally like the default firewall, pf. It’s got a bad reputation in some circles though.

No systemd.

No systemd.

No systemd.