The sorry state of medication reminder software

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I use an app called Medisafe to give me my medication reminders. It’s useful because it tracks my doses and also tracks how much I have left so I know when to order refills and so on. I’ve been using it for years.

Unfortunately it has a critical problem in that it only sends three easy-to-miss reminders spaced ten minutes apart with no way of configuring it. So often I’ll end up taking my medication a few hours later than the scheduled time, because I head to bed and notice the pending reminder that I meant to fulfill.

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How the heck I can listen to music the way I want to

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Okay, after posting my rant, someone on a Slack I’m on pointed me to Smart Shuffle, an alternate player for iOS which plays music the way I want to listen to it. (Thanks, Roman!)

I also signed up for iTunes Match, which provides the only part of Apple Music I care about (while also costing way less). And it seems to be doing a good job of pre-populating my device with music, and Smart Shuffle is able to play from iCloud while I’m on wifi and then automatically switch to stuff that’s locally cached when I’m not on it, so hopefully that makes for a reasonably seamless experience.

I guess with the vast quantity of music I have at this point I don’t really care about play stats for excluding stuff I’ve heard recently since I have so much of it that it’s less likely for duplication to happen like that.

The iPhone does have a setting for how much music to prefetch but as far as I can tell there’s no way to tell it which playlists/songs/whatever to prioritize; as far as I can tell it intends to focus on stuff that I listen to already, which is pretty much the opposite of what I want.

I suppose that if I care incredibly deeply about having proper randomness available on my phone I could just get a 512GB iPhone when I inevitably upgrade. I guess that’s a decision I can make next time I’m in Portland (which is in just two weeks).

One annoyance with iTunes Match so far is that it refuses to cloud-upload songs which it sees as duplicates. Fortunately its duplicate detection seems to be a lot better than in the bad old days of just matching artist and title, but unfortunately it still means that if you have an artist who has released multiple close-enough-to-each-other versions of the same song on different albums, or has released a best-of compilation, you’ll only get one rendition of it and it won’t appear in all the albums, and you can’t even choose which one is the canonical album placement. Kind of annoying. But less annoying than all the other things iTunes annoys me with, I guess.

How the heck can I listen to music the way I want to?

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I collect music. Lots and lots of music. I have something like 250GB of the stuff. It’s across basically every genre known to man. Possibly a few unknown to man, too.

The way I’ve preferred to listen to music for the past 15 years or so is to have my player device of choice shuffle by album - which is to say, choose an album at random and then play it all the way through, in order. It works really well for my listening habits, because it ensures that I will, for example, get a complete opera (following all of its cadences), followed by a complete rock album (following all of its cadences), followed by a complete abstract electronica compilation, and so on. Sometimes I’ll get singles interspersed between them. That’s fine.

The main way I discover more music is if I come across something I like (from random YouTube exploration or adding the SXSW torrents to my library or whatever), I will just buy that artist’s entire discography all at once, with the hopes that those albums will eventually come up in my listening sometime in the future. It’s like a little present to my future self.

Unfortunately, the modern music app landscape makes this incredibly difficult to do. Back in the classic iPod era, this worked well enough - I’d make a smart iTunes playlist which just filtered out stuff I’d listened to recently, and then populated with random albums up to whatever storage limit the iPod had. (Once upon a time I could fit my entire library into a single iPod Classic but that hasn’t been the case for well over a decade now.) And I continued with this with the iPod Touch and iPhone and so on, because even though those devices didn’t support shuffle-by-album, the smart playlists still worked.

But now a few stupid things have all happened:

  • My iOS devices stopped being able to sync (and none of the “fixes” I’ve found work at all)
  • iTunes switched from being a “manage your library” thing to an “Apple Music frontend player”
  • I tried using iTunes Match to at least get the iCloud Music Library thing but now that’s made it so that even my smart playlists don’t work anymore – even after disabling iTunes Match! (In particular, they no longer shuffle by album and I’m no longer able to force it to re-select a new set of songs, which I used to be able to do by removing items from the playlist.)

For years I have stuck with iTunes and iPod/iOS because they were the only ecosystem I could manage to get to work right with my listening preferences. I haven’t found any other players, much less device synchronization systems, that allow for the shuffle-by-album thing. But now even that isn’t working anymore, and Apple is showing no interest in fixing it; I’ve had bug reports open for years on each of the individual issues I’ve mentioned above, and nobody I know seems to run into these problems but nobody I know wants to listen to their music in this way; they’re happy to just listen to random radio/Apple Music/Pandora/etc. stations, and don’t care about plumbing the depths of their gigantic, varied collection.

I keep hoping that someone will know of some alternate player and sync solution that lets me do what I want though. Every now and then someone will maybe mention that there might be a Foobar2000 plugin or something but I’ll look into it and not only is Foobar2000 Windows-only but it doesn’t actually do what I want, or it has no way of synchronizing with plays across devices or whatever.

I’m not even asking for anything that exotic or unknown. iTunes used to do this as its normal mode of operation. But it’s like everyone who makes music software and library managers has forgotten about everything, possibly because of the streaming services which are in turn patterned after radio, which never provided a listening experience I enjoyed.

I’m not about to start hand-managing my library either. My brain isn’t nearly large enough to keep track of what music I’ve listened to or make the decisions of what to listen to next. I want a simple unbiased random algorithm to do that for me!

Why is this so fucking hard?

EDIT: It looks like there are macOS and iOS versions of Foobar2000. The macOS version is outdated, abandoned, and doesn’t support album shuffle (or external device sync). The iOS version supports album sync but just uses the iTunes library on the device, which is great if you can sync music into it but I can’t. So frustrating. But it looks like maybe there’s a way that I can sorta bludgeon it into working? We’ll see.

EDIT 2: So of course right after I posted this, iTunes suddenly started behaving again. Let’s see how long it lasts this time.

Also someone on a Slack I’m on wrote:

Perhaps it’s time to concede that whatever you want from it is just not going to work reliably any longer, and adjust expectations and habits accordingly? It’s quite obvious that it’s not going to get fixed anytime soon.

Nah, fuck this attitude entirely. I’d have to completely change the way I listen to music, and all of the ways that are even feasible anymore are the ones which just so happen to help the record labels instead of actual musicians, for some reasonGee golly whillikers.

I am so sick of control being taken away from me, especially in a way which doesn’t benefit the musicians I want to support.