Problem syncing tones

Biting my lip and trying to forego how much I find iTunes to be the more ridiculously terrible, frustrating software in mass use...

But hopefully, there's something "Apple simple" that I've missed and you can help. I've drilled through the community as well as lots of third party sites, nothing consistently addresses this issue in particular, and even the responses here to very similar situations are all over the map and full of non-intuitive workarounds to get tones syncing. Why can't we just put what we want on our iOS devices? Why must everything be in a proprietary format and iOS will not even think about handling others? Why can't we have removable memory and batteries?

Whoops.

Anyway, THE PROBLEM: I can "drag" "Tones" into current version iTunes, they show up under "Tones"... but none are playable in iTunes, nor will they sync to the iPhone, no matter what.

Fig.1: iTunes "Tones" page in the "On This Phone" library. Note the weird little marching ants circle in the first unlabeled column--what does this even mean?

Some important notes:

I've selected, sync'ed, unselected, re-synced, (and repeated probably 20 times throughout my testing options below, and carrying out these various other things that were recommended here and on other sites). This makes no difference. However, I do leave it set to sync "Tones" in the end.

I've checked, synced, and unchecked, synced, etc. etc. the "check mark" on these to no avail.

I've made the "Tones" with special apps, as well as the standard i-Way-or-the-highway-method, both ON the iPhone with third party apps, and on the PC. I've also done the create an AAC version, and rename it to M4r thing. All ring tones are sub-40 seconds (I also made some sub-30 just to be sure).

I've dragged the files into the "Tones" list (as well as into the left-pane library list thing) using unmodified drag & drop, as well as tested for all combinations of the secret, undocumented ALT/SHIFT/CONTROL drag & drop options. The only difference is with SHIFT it says "Copy" instead of "Link" while dragging. They always get pulled into the "Tones" list/library, but always, they're just unavailable.

I've removed (deleted from iTunes) and re-added these, and other "Tones" multiple, numerous times.

I used the Apps > File Sharing > Documents method with apps designed for this purpose also to no avail (and really, how backwards and hidden/non-intuitive is this approach???)

I'm using iTunes 11.4.0.18 on Win7/64 in this case with an iPhone 5s running iOS 7.

• & Yeah, upgrade, you say? Hrmph... no way I'm eliminating my chance to jailbreak this bound-up, locked-in, compartment syndrome OS. If that's the best answer you got, I'll live without all of my custom "Tones" or go back to WM or Android where things are actually usable, and I'm in control of what gets put on my device.

I had numerous "tones" with previous iTunes versions. This seems to have only been a problem with recent iTunes for me.

Before you tell me to right-click and do this or that, here are my right-click context menu items:

• Play [Song]
• Get Info
• Rating
• Show in iTunes Store
• Delete
• Uncheck Selection
• Apply Sort Field.

If I hit "Get Info" to look at the file properties, almost everything is unavailable ("grayed out for you visual-oriented folks"). for what that's worth.

Also FWIW, the File > Create New Version > Create AAC Version option is unavailable/grayed out in case that's relevant.

Is this some DRM issue because these "Tones" were not purchased form Apple's iStore or made from songs purchased from Apple? If so, that's pretty DUMBUH.

Okay, hopefully that covers what I've tried according to randomly scattered "hints" and uncollected thoughts from forums here and abroad.

Obviously, I'm not a fan of iTunes. It's the most frustrating software I have to use, as a consumer--and I remediate software for a living, so I work with a LOT of horribly frustrating software. If that makes you upset, fine, don't contribute to helping, but don't waste our collective time defending it without a solution because you think i-devices are cool.

Please show me how I'm just missing some mundane non-intuitive detail, and iTunes will get .0002% more respect from this guy.

Thanks for any and all fish.