One of my goals for this year was to improve some of my digital setup. Some of that is for photography, some of it is for astronomy, a few other things here and there, but the three big “techno” areas for me this year are my laptop/writing setup, my TV subscriptions / antenna options, and my audio files. Namely, my music collection in digital form.

I’ve been delaying a deep dive into the world of MP3 management for some time, partly as I’ve been burned before. Several times, I thought that I had found a solution, everything seemed to be working, I was making some progress, and then BAM! The app stopped being supported. Or I had a crash and lost a bunch of work. Not the actual music files themselves, I’m pretty good at backing them up, but having a good file structure with a good management program and a player? Not so much.

I used to love programs like WinAmp. Simple interface, could handle the synch with my iPod well, heck it even would synch with a Sony Walkman (yes, they used the name for a small line of MP3 players at one point too, and because it is small, lightweight and functional, I still use it as my music player of choice when portability is the main factor). I almost never use my phone or tablet for music playback as it is just a license to suck battery life. I’ve struggled with ripping from time to time, finding a good setup, good parameters that didn’t produce overly large file sizes that I wouldn’t notice the benefit of cuz I have basic system for playback and no real discerning ability with my ears. I have an old boss that has more money tied up in high-end audio WIRING then I have in my entire stereo collection.

But I was determined to do it right. Now, just to be clear, I wasn’t looking for a perfect solution, nor even a solution to a “problem” per se, I was just wanting to update my approach, maybe find some baby steps that I could take. Wow, was I in for a surprise.

50,000 reasons to hate iTunes

While I was starting to figure out how I wanted to sort my library with as few “layers” as possible, I updated iTunes just to keep it up to date. It is after all a good store. I had pushed everything over there in my last go around about 18 months ago, and I had decided pretty much at the time to go all in on iTunes, right up until I noticed a couple of files seemed to “change” quality and size after I synched with iTunes. It seemed odd, so I started looking at it more closely. In addition, in one case, iTunes even changed the filenames of two files — assigning the song name for Track 7 to Track 8, and visa versa. Weirdness in naming and how did some of the files shrink? WTF?

I then starting looking around online and found out that iTunes has a unique little feature. By default, when you synch, if it finds the file in its library, it doesn’t “upload” and save your copy. No, it just uses its copy (to save bandwidth and file size). No biggie, right? Except it then goes a step further in the synch and REPLACES your copy with the file from its database since it knows it is safe and sanitized. Which isn’t a huge deal if the files were the same…except they weren’t. I had ripped at a higher quality than the iTunes version, so my files were originally larger, and now they were “downgraded” to a lower quality and smaller size. Would I notice? Probably not when actually listening, I don’t have an audiophile’s ear nor the equipment. You can turn the setting off with a little tweaking, if you know to even look for it, but the default is to replace all existing files with the iTunes version. I found a few horror stories online where someone had some specific backups of old recordings that got replaced by iTunes with no warning or notification, and after a couple of subsequent backups not knowing there was anything wrong with the originals, their backups were now just the iTunes version. Bye bye sweet memories, hello commercial pablum. While these problems stood out, there were lots of other quirks people had found and posted online, and it made nervous enough to want to manage my music files myself without an auto-synch taking over. I manage my ebooks the same way — myself with my own software, not Amazon’s or Kobo’s or Nook’s, etc.

So my commitment to iTunes was done, and it slowed my music-organizing work in 2015. I tried Music Bee, but it wasn’t really jiving for me, and I eventually completed stalled. Until this past week, when I got back into it. I checked the iTunes install, and now it was REALLY weird. While I had some 3500 files stored in the iTunes media folders, only 35 were showing up in the actual iTunes app. I had them all in there before. I had done massive work to upload, sort, tweak the meta data, etc. Gone. So my hope of exporting and importing was gone. No biggie, it hadn’t been finished anyway, and I wasn’t sure what I was using now anyway.

Except then I noticed another problem. Those 3500 files. It seemed like a lot, well structured, but there were a few odd things missing. Like Jacob’s kids songs. I had four or five CDs ripped, and they weren’t there. Then I noticed some collections missing from the 1940s and 1950s. WTF? Where are the rest of my music files?

I had told iTunes back in the day that it could have permission to manage my music folders. Which meant it imported everything from another directory that was a bit chaotic. I never noticed at the time, too busy working within iTunes to notice that when it imported it into the directory, it DIDN’T actually complete the job. I knew it hadn’t uploaded everything, and in fact I hadn’t wanted it to until better organized, but I thought it had at least COPIED everything and that it was now all IN the directory. Nope. Not even close. I have another 40K files that just aren’t there. No, not another 40K songs, there’s a lot of chaff in that mix, with lots of duplicates, but probably another 10K active songs. I knew they weren’t in iTunes, like I said, but they should have been in the iTunes media folder. Nada.

Small panic. Maybe they’re elsewhere in the drive? Nope, I cleaned those up LONG ago. Cuz iTunes had them, no worries. Except it didn’t. So I checked my backups…of course, 18 months ago, my backups would have had those secondary directories. But now? I’ve completely rolled over 2 or 3 times since then. So my backup is JUST what iTunes has. Yikes. 50,000 down to 3500? That’s a big reason to hate iTunes a little, even if it isn’t entirely iTunes fault (I should have verified that it copied what I told it to copy!).

Digital packrat

I dug out two old backup drives, ones I’m loathe to just ditch even if they are not part of my regular backup routine now. I loaded them up and started working my way through them. One was relatively empty, easy to wipe and set aside for a future secondary or tertiary backup of some key files (it’s a 500GB drive but requires power, so not simple USB mobile device). The second is a 2TB workhorse. Killed tons of crap that I don’t need anymore, long since improved or reorganized, but then I found my old music files.

They’re relatively a disaster in terms of organization, no question about it. But the extra files are there. Some overlap with what I already have, but surprisingly not as much as I might have thought. What did I find? 3000 folders, 40K of files and 160GB of music related materials. Ah, so that’s why my Music backups didn’t take up as much time or size as I would have expected. I should have twigged to it earlier, but I trusted the wrong app.

Which means I have to copy all of those over, sort them, and figure out what I’m going to do with my new apps.

New apps

I mentioned that I had Music Bee for awhile but it just wasn’t “singing” to me. Then, with a cellphone plan that I have, I got Spotify for free for two years. Instant music, no need to organized, synch, or do anything else. It was just there. Or at least it is there for two years in total, another six months or so. I’m not totally comfortable with subscription based music consumption, partly as I don’t use it anywhere near enough to make it worth it, and at the end, you don’t own anything. It is just “temporary”. Why rent when I can buy?

Except of course I need to rip a lot of stuff, and I want it in a good format so I only do it once. Plus I want to be able to upload it somewhere where I can access it via the web. Oh, and I want to be able to synch to my Walkman, play it on an old tablet connected to my stereo, and just for fun, synch the music to an old iPhone or two. Easy peasy, right? Let’s break it down in order.

For the streaming, it is relatively easy. While there are a number of apps and sites, the three biggest are Spotify, Google Play Music (GPM) and iTunes. I already ditched iTunes, and I already have Spotify but it isn’t doing everything I want nor does it have great options for my own music so much as just using their existing library. Which means those two are not high on my list.

Since I use Google for everything anyway, I started looking pretty heavily at GPM. I can upload up to 50K of my own songs. And then I can stream them. And it’s free. If I want to upgrade to the full streaming system, it is $10 and I can have up to 10 devices. Colour me sold. Why didn’t I do this LONG ago?

So that left me merely with finding a good music manager for my desktop. Most of the big ones would work fine, and most of the real differences between a lot of them are graphical user interface choices. I prefer a simple list layout, something relatively like Windows Explorer even. But the real kicker for me is to where I want to be able to transfer the music. I almost never listen on my PC itself, partly as it is in a shared office with my wife. Instead, I want to be able to transfer it to six separate devices:

1. My Sony Walkman — as I mentioned, it’s an MP3 player that Sony slapped the Walkman rubrique on for branding, but it is small without being like an Apple nano. Good size, works well, good battery life. I load it up with my music and then it sits on there until I get bored with it and want something else. Not very quick to be changed, I mean. But I want the app to recognize it;
2. My old iTouch — I have an old iTouch, and I want to be able to just dump a ton of stuff on to it and plug it into my bedside clock radio/stereo. I could stream off of Google Play through my network, but really I just want it to be a physical storage device with direct loading; and,
3. Andrea’s old iPhone — she has an old iPhone 4 or 5 that had a cracked screen, so I got it repaired with the intention of giving it to Jacob as a simple camera and portable app toy. The synching with iTunes for apps isn’t very functional though, with the software getting a little long in the tooth, so I’m looking at repurposing to be another portable music player. I’m also going to try using it as an underwater camera in one of those sealable pouches, and well, if it dies, no great loss;

The other three are a bit different though as they are three fully functional Android devices, which means I can either stream or synch with them direct.

4. My phone — I have a 32GB SD card in it, so I could just copy it over. Or I can run the Google Play Music app. It would be great though if I could synch wirelessly with my phone, the way I do to upload my photos when I want to transfer them to the PC;
5. My big tablet — My newer tablet is wireless, and like my phone, I can either synch the music and carry it with me on the SD card or I can just stream GPM. But either way, it would be great to synch wirelessly with the PC; and,
6. My old small tablet — I have an older slower Samsung tablet that is basically collecting dust in my office. It isn’t fast, it isn’t fancy, but it still runs everything on Google. So my plan is to copy everything over, either wirelessly or not, and / or install GPM on it, and hook it up to the computer in our family room. Instant stereo feed.

Now, with those six devices in mind, I fully expected I would not be able to do it with one app. I thought, “Okay, one app to synch with the first batch” and hopefully I could find another that would handle the second. Or I could just use GPM to stream it. Except as I was reading online of the top 10 music managers from 2016, I came across Media Monkey again.

Media Monkey

I had seen this app before, back in the day, and I ended up with Music Bee and iTunes. But as I went through a good review over on Tom’s Guide of music managers, I was dropping some of them fast. Won’t synch with iDevices? Gone. Trouble with other MP3 players? Pass.

Wait a second. It says Media Monkey will synch with regular MP3 players AND iDevices? Hold the phones — it will also synch with Android WIRELESSLY? Holy cow, that sounds like the perfect app.

Sure, it’s a bit of a pig for display, a little small here and there, without much opportunity to fix it. The skins are terrible (had to revert to Windows). But it does have a file tree-like view option. Text for the rest. Recognizes my Sony device. Synched wirelessly with my phone.

And if I rename a heading in the music view, it renames the actual folder in the hard drive. Outstanding.

This will bear some careful examination, but I think I’ve found my tool.