Linux

No.

If you ever so carefully paint yourself into a corner then the corner is where you will be stuck. How badly do you want out of your corner?

There are FOSS and SAAS options that could work if you wanted them to... but whether they will depends on you.

Meat eaters trying to become vegetarian for ethical reasons often fail because the "un-meat" options out there don't meet their standards. Success almost always requires some letting go and re-adjusting. If you are not open to that then don't force yourself to put up with something you don't really want.

Full disclosure: I ran manjaro as a daily driver for a while a few years back bad have been forced back on windows as well by company policy. So I'm not going to be the ultimate authority to answer your questions.
All I wanted to comment is that with iTunes and Office you have picked two pieces of software by two companies that have a very strong interest in not letting you migrate away from them. I tried to migrate my gf's password manager from the iCloud one to bitwarden and it's amazing the hoops they make you jump through to get at your data. So what you might be experiencing right now is a thing called "vendor lock", and I wish you the best of luck for finding a way out. ;)

Some of these are going to be a bit of a challenge, but let's put down some keywords you can look into.

1. Airsonic or jellyfin in a docker container

   • I also recommend a container with lidarr etc. and a qbitorrent locked into a VPN
   • smart playlists may take some playing around with, however playlists are just a text file, so in a pinch a python script will do basic things.

2. This one's easy, I use rsync / unison with termux, there's also syncthing.

   • No clue with Apple. Jellyfin and airsonic stream well to it though

3. Nope, if this is a deal breaker, stop now. If your flexible however:

   • Excel: python, Jupyter, R and libre Office
     • Rmarkdown will produce reports
   • OneNote: Joplin, Obsidian, Dokuwiki, tiddlywiki etc (see r/pkms on Reddit)
   • Word: markdown with vim, vscode Emacs and then pandoc

4. Immich, shotwell, F-spot photoprism and I think there's another KDE tool that has AI

   • I'm very happy with immich, it does require docker, which is worth it imo.

5. Scanners do work, but I don't know how you'll connect it with Evernote.

Don't have a lot of time right now... But if your iTunes library is DRM free music files (Apple moved new purchases to DRM-free some number of years ago when Steve Jobs was still at the helm, however if it's a song you've had a really long time you might have to pay Apple for the DRM-free slightly better quality music file), you're in good shape with something like Rhythmbox.

On the office side... I'd try using the LibreOffice suite on your current operating system instead of office and see if you can get away with it. It's the best open source office suite around ... and it's cross platform, so you should be able to tell if that's going to be a problem without going all in.

I think the key is you need to find FOSS software that works for you before migrating your OS. Most FOSS software will run on windows and sometimes MAC.

1-2 and 3 will be hard. You can find many tools that do something similar but it won’t be perfect. There are a few different music managers, and for office libreoffice is the go to.

4. try digikam, it supports all OSes

5. googling “Fujitsu snap scanner Linux” yielded a few blog articles on the matter. Seems it should be supported.

Before I migrated, I had devised elaborate lists of programs and things I thought I would always want with me. But now, years later, looking back I realize that most of those list items had been replaced by new stuff that I found I like even better, or simply dropped from my routine altogether as I grew to realize they weren't actually all that essential.

I went local with my music collection.

I'm not sure if it ticks all your boxes. But there are many options for subsonic servers and clients - you can probably give it a good test run on Mac/iPhone as well. I managed to migrate from spotify painlessly enough to pass the wife test.

I'm running navidrome as server and tempo on my phone. It'll either stream from my self-hosted server, or play offline if I've downloaded that playlist.

I'm sure you can find apps that do smart playlists. Metadata and regular playlists are easy, though you may need to do a little work to script some kind of conversion.

Outlook doesn't have a Linux equivalent at all. Thunderbird is great, but it's a downgrade. I'm not sure how well it would work through Wine or similar. What's keeping you from OWA?

I think most people use Immich or Photoprism for a local image management program. Try [email protected] for more alternatives.

Any scanner program should be able to scan like you want.

I've never used it, but Crossover Office was developed largely to get MS Office working on Linux. It looks like it's still maintained.

It's at least worth looking into.

Those 5 requirements are not small things, but as a (relatively) recent linux migrant, here's my take.

1. Keep using iTunes (but use the windows version) - through wine. You get to keep all your stuff as is for now with the possibility of migrating to another service in the future.

2. See above, stick with your current device, keep using iTunes for now.

3. If it's for private stuff LibreOffice suite does just fine though + the thunderbird email client. If it's for work you should probably have a work device, but there is also winapps for linux, which isn't official by microsoft, so it might be a bit funky.

4. Maybe try out proton if you want something trustworthy to back up your photos. They've recently added a service for that. Costs a subscription though.

5. Keep using evernote. There's a linux client.

Obviously there will be hickups, and things'd be a lot more smooth if you were willing to make some adjustments, but this is perfectly doable.

1. I use rhythmbox, but my usecase isn't quite as extensive as yours. I don't think it has smart playlist capabilities, for example. But it is able to rip MP3s from CDAs, which is cool.

2. I haven't found anything that will work 100% with iphones on Linux, but I no longer have iphones, so it's been a while since I've looked.

3. MS Office used to work fine enough under WINE. I've had 0 luck with 365. There's LibreOffice, which is a great replacement for most things Office (minus Outlook). Thunderbird, I think, has an exchange plug-in. On my home computer, though, I use Outlook web, which has worked just as well as Desktop for my use cases so far. I understand you want Desktop Outlook, so this may be a deal breaker. However, Desktop Outlook New is heading towards WPA anyway, and MS is trying to sync the functionality between desktop and web, so this may only be an issue for a little while.

4. I don't have this use case for my computer, so I can't really help here. But others on this thread seemed to have provided some nice options.

5. not sure you'll get integration into proprietary software like Evernote, but there are built-in scanning tools that "just work" with every scanner I've thrown at it thus far. I do not have the same scanner you do, though.

I recommend grabbing a live ISO of a distro you're interested in trying (Mint seems to just work for most people, ElementaryOS if you want to maintain that macos look/feel), and just trying it out on RAM. No installation needed, and you can get a better feel if this will work for you. Don't expect a perfect fit, though. Workflows and solutions will differ from Mac to Linux, just as they do from Mac to Windows. This was one of my reservations, and why I kept finding myself back on Windows and Mac. The end goal, IMO, should be to get out of the walled garden in which you've found yourself. Once I realized that, once I switched my goal from 'finding exact replacements' to 'getting out', switching was much easier and smoother. Good luck! Post any questions you have, and we'll do our best to guide you right. This is a great and super helpful community (mostly lol).

Hi there and congrats on giving the idea of migrating towards digital freedom a go.

I personally havent used macs ever but am on ios still for my phone and was on windows before with outlook, excel and word.

What I did was the following:

Entertainment

I run a plex server that organizes my music library and plays my music on all devices. Some things like sonos still have some issues with flac files but otherwise, playlists and albums are no problem. I dont know how strictly you need everythin on device because apple doesnt let you do that on linux without hacking itunes to run on wine. I stream music from my server and it is always reliable as long as I have minimal connection. There is a download option but I havent tested it. Movies play with no issue.

Office

I fully transitioned to libreoffice on devices and use collabora office with my nextcloud instance when I want to cooperate over cloud services. Outlook has been replaced by thunderbird, events go through nextcloud, synced over all devices.

Photos

Also nextcloud. I sync all my photos between computers and my iphone. Nextcloud is work to set up but it is imho the most integrated solution which gives you a pretty comfortable experience. You can host it yourself or pay someone to host it for you which of course would mean a lot of trust that is needed.

Bonus: security

For the sake of my sanity, my private stuff stays on my home network and the only way in is a vpn which I have automated on my laptop and a linux phone that I‘m working on. Ios afaik needs manual activation but once its synced, you‘re good. That takes the biggest threat away from personal cloud hosting imo. Just secure your home network and there should be no issues.

Let me know if you have any further questions.

P.S.: I would suggest you first build the infrastructure. An old quad core with 8 gb ram, gigabit wired network and two good nas disks in raid 1 with an encrypted off site backup gives you double redundancy.

The last time I ran desktop Linux I recall the default music player for KDE being closest in functionality like ratings smart playlists a shuffle mode to select an album at random and play the whole album in correct track order. Looks like "search playlists" in Juk might be the feature you're looking for. But I can't recall much in terms of mobile syncing from then.

I'll assume you have already, but did you look at Plex Amp on Mobile?

For Office, if Evolution can't do what you want then I'd say to try MS Office under Wine.

Someone else already suggested DigiKam for phitos. I've looked at that a little for replacing Lightroom.

1. you could try Plex and PlexAmp. I believe you need to buy PlexPass but that can be a one time fee.

2. if it hasn’t been mentioned then Immich is by far your best option here. I’ve tried most of the others and there isn’t much comparison in my opinion. Native mobile apps for iOS and Android are available. Browser for viewing from desktop.

I started using FOSS apps on OSX until I got familiar with them, then moving to Linux was a lot easier.

There’s a lot of people in this thread saying it’s possible, some saying it’s not and more than is really healthy saying there’s something wrong with you.

But the question I can’t help but ask is should you switch to Linux.

I don’t think so.

You’re trying to get away from the high price of Apple hardware, not out of a general unwillingness to pay for expensive things, but because the ram and storage in the computers are no longer upgradable.

To do so you’d have to find bespoke solutions based on new software and systems you might not be familiar with and which mill most likely face loss of maintainers and updates some time in the near future.

That’s not a dealbreaker really, but the general trend in laptops is moving away from replaceable memory. Sure at the moment you generally can still replace the disk, but for how long? Are you thinking that apples ahead of the curve on system on chip devices or that they’re making a misstep? Personally I think anyone your age or mine will have a hard time buying new computers that don’t have everything built into the board or processor before we shuffle off. I could be wrong though.

Let’s say it doesn’t matter though, just in dollars amortized over the life of the hardware, how much are you really saving by upgrading the memory and storage?

I tend to run five + year old macs and for the oldest ones, the 12 year old MacBooks, I got lots more life out of em by doubling the installed memory to 16gb and going from hdd to ssd. How much money was really saved though? Maybe ten bucks a month at the most.

Are you keeping em for fifteen years or cycling out every five or so?

Newer Macs which already have ssds don’t see near the stark performance change that we probably both wowed about when going from hdd to ssd.

You’re not really listing any software or operations in your post that would make upgrading the ram from the (maybe?) current 8gb minimum to anything more seem worthwhile.

It’s not that I don’t think a person could do what you want to do under Linux, just that it doesn’t seem like something you ought to pursue when weighed against the relatively low cost of just staying with the system you’re using considering the computers themselves will hold value better over time than anything you might swap out to.