> I know it was not your intention but your comment reminds me of the infamous HN comment on why dropbox is useless and would never be successful.[1] :))

Except the context of the argument is different. OP is doing this for convenience and privacy reasons along with the availability and no-cost argument. While it's a slight point to make it is an important one these days. With the Dropbox argument the old HN comment was making the point without the context of privacy, security or even availability of which we all have to consider today. We know service providers have removed or deleted purchases by users. Some providers remove content and make it paid for during adventageous times of the year (e.g. holidays) and, well, privacy doesn't need much expansion here. We also know vendors can lock you into hardware ecosystems through file formats. Finally if we all stop DIYing our media/files/etc the options will turn into expert level oniy. So the continuation of this being a thing keeps the open side of the conversation right side up. Lest we all end up boiled frogs.

The last sentence of that comment is:

> I know this is premature at this point, but without charging users for the service, is it reasonable to expect to make money off of this?

I googled for 'dropbox financials', and soon ran across a TC article about its IPO last year [1] which says:

> The company’s prospectus warns it has “a history of net losses”; anticipates increasing expenses and slowing revenue growth; and notes that it “may not be able to achieve or maintain profitability.”

I'm still not sure that snarky 10-year-old comment was far off.

[1]: https://qz.com/1214822/dropbox-is-filing-for-a-500-million-i...

Dropbox has been operating at a loss since its creation and is currently not making a profit, so the jury is still out on whether it is actually successful (or just a VC-subsidized service that got advertised a lot).

You are correct, but the metrics of success have always been different in tech. Regular businesses would be considered failures if they had 10 years in the red. But if you get a "unicorn" valuation and manage to IPO without even making a profit, well, that's the dream for a lot of HN'ers. If somebody out there makes you a multi-millionaire based either on faith in your company or in their ability to shift the risk to the next sucker, who're you to say no?

This gives me concerns about legacy. Henry Ford is still well known and quoted today not only because he built a well known company and iconic products a century ago, but because his company is still building cultural icons today (F-150 and Mustang).

I would much prefer to build a Ford than a Yahoo/Tumblr/Compaq, even if it meant my personal fortune was 10x or 100x lower.

>the metrics of success have always been different in tech.

It hasn't always been that way at all, but it certainly is now. I think this is one of the huge red flags about the modern incarnation of the tech industry.

Agreed, "always" is the wrong term. "Since the late '90s" would be more accurate.

This comes up all the time and it's silly.

If dropbox only had a high valuation on paper, but employees/founders/investors couldn't actually exchange that into real $ in their bank account then sure, you can say the jury is still out.

But that's not the case. They built a product, have tons of paying users, and have IPO'd with a market cap over $10B. It's not money that only exists on paper. Founders and employees can sell their shares for real money and buy real things.

Their shareholders aren't just a handful of VC's anymore - they are public. The jury has decided, it's successful

> The jury has decided, it's successful

Hypothetically, what if it never begins earning more money than it spends each year? At some point wouldn't it be unable to borrow any more (from banks or investors) and be forced to shut down? And if so, we still don't know if it can be profitable, right?

It’s successful to me as a user. Beats the heck out of that whole “set up an FTP server” recommendation. And how much is their loss due to growth focused investment?

My setup is far simplified from the parent's--I simply have all my music backed up onto an external HDD that is attached to my HTPC (roughly 2TB of MP3s and FLACs). The "Music" folder is shared over the network via the Windows share option, and all of my Linux machines are able to trivially mount the directory as well using a SMB/CIFS share.

There's so little effort required that I'd barely consider it a DIY solution, considering that most of the OS's can see it and access the drive without leaving the file explorer.

I also discovered it happily continues to work when my ISP had an outage, since all of the IPs were local and still accessible provided that the router was up.

Actually, I'm rather shocked that there isn't an all-in-one solution like what I've cobbled together. It's not like there's any super secret magic involved; you'd just need a nice user interface on top of it all.

There are even music streaming servers that you can deploy on a VPS (or locally) pretty easily. Pop in a little rsync script to move your converted lossy files to the streamer and you're set. It's just that nobody's built something that integrates everything yet, thus my Frankenstein setup.

You'll be surprised, but AFAIK Windows Media Player can do all of that.

Media Monkey does all of the things you mentioned, and with a GUI. Rip, store, convert, transfer.

I'm pretty sure there are Synology applications that also do what Plex does and with a nice phone app.

Have you heard of Plex?

Plex doesn't convert files for storage on a portable device, nor does it replaygain. It also has a terrible music selector interface and doesn't firewall punch.

Streaming is only part of the issue. I'm talking about the whole lifecycle, from backed up lossless to lossy-on-device in whatever format, or to a streaming service that integrates with your player devices, all from a single source of truth that you control 100% with no silly DRM or ads or restrictions.

>Plex doesn't convert files for storage on a portable device

Yes it does, you can pick what quality you want when you sync[0]

> doesn't firewall punch

It does so via a reverse proxy if required[1]

[0]https://support.plex.tv/articles/201053678-sync-media-to-a-d...

[1]https://support.plex.tv/articles/216766168-accessing-a-serve...

I know it does encoding/decoding for video at least; I don't know how its music features compare.

> Plex doesn't convert files for storage on a portable device

I don't know about Plex, but Kodi does this.

As much as anyone that gives tech support to their parents I can assure you I get your very fine and subtle irony.

In systems development, the KISS principle (Keep It Simple, Stupid) is precious, it is your safeguard to mental and emotional health.

As the MIT / New Jersey schism taught us decades ago, there is no one concept of "simple". Simple in design? In implementation? For the user? For the architect? To set up? To troubleshoot?

Which is simpler: a pile of files on a hard disk, or a playlist in an online music service? It depends.

It's like asking what's the simplest mode of transportation: a 1985 Toyota, a 2018 Toyota, a Lyft, a bus, or a bicycle. You could make a good case for any of these, depending on your situation. I know people who can't operate a manual transmission, so the 1985 Toyota would be problematic for them, but on the other hand, I've never fixed a 2018 Toyota (or a bus) with just the tools in my backpack and a water bottle.