Stuck in Mac Purgatory - cannot delete files

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You have so many problems that I would recommend you to format and reinstall OS X again. By doing this, you will get a fresh copy which should run properly and you will be able to upgrade OS X to OS X Yosemite if you want to, but first check that your hard drive is working correctly.

To do this, press Command and Space keys to open Spotlight and type "Disk Utility". Then, choose Disk Utility and select "Macintosh HD" (or the name of your OS X partition) in the sidebar. Finally, press "Repair disk permissions", and when it finishes, check that you can delete files. If not, press "Verify Disk" and tell us the results.

If the hard drive is OK, I recommend you to reinstall OS X. Read -> Mac OS X v10.6 Snow Leopard: How to Erase and Install - Apple Support As you mentioned Time Machine, I suppose you have a backup, but if you do not, make one.

User File Ownership - Reset see post by Linc Davis

Hi Falconer.

It shouldn't be a Time Machine issue, (unless you set a part of your HD as the Time Machine drive.

How did you ascertain that it was specifically old photos/podcasts that you already deleted?

iPhoto

Have you emptied the trash folder within iPhoto? iPhoto's Trash is not the same as the system's trash, so you have to ensure that's empty too.

iTunes

When you trash stuff from iTunes, it normally just sends them to the system trash, but you have to then empty the trash, although it sounds like you've done this multiple times already. Are you still seeing those old podcasts actually within iTunes?

Versions

I can't remember whether Leopard uses 'versions'. That's Apple's replacement of 'Save as'. Do you use any software that has in the File menu, the options 'Duplicate' and 'Revert To>Browse all versions'? Versions has a front-end that looks exactly the same as Time Machine, but these 'snapshots' are not stored on your Time Machine backup, but instead locally, and they can fill your HD over time if the system doesn't delete them. I reclaimed over 300Gb of HD space after deleting old versions using OnYx.

Disk Space - Free Up

Disk Space – Free Up (2)

Disk Space Filling Up – OmniDiskSweeper

Disk Space Filling Up - WhatSize

Everything you describe seems abnormal to me.

The need to 'double delete' is not right, the duplicating files is incorrect the lack of free space is a real concern. If you have no free space at all the OS can get into situations where it cannot work correctly. The only files that should give you trouble in deleting are system files that have restrictive permissions and Time Machine backups. Time Machine should have no data saved on the internal disk, so it's possible you have misconfigured Time Machine if it is creating backups of the boot disk.

I strongly suggest you find a way to take a full backup & then clean install 10.10 if you want to use that OS.

If you have another disk large enough to contain the Mac's data you can boot into recovery mode & use Disk Utility to make a full bootable copy of the Mac onto the other disk. This OS seems to be beyond your abilities to repair, a fresh start could be a good thing.

Do you want a description of how to backup in recovery mode? I realise you need to clean up this Mac to be able to backup iOS, but at this stage it seems that you have no recent backup of the Mac. It may be time to erase, start over & then copy your user files back to an OS that works.

You mention only a single hard drive. Can you confirm that you have not been backing up to an external drive? If you have not been backing up to a second drive, you have been creating this situation over time by backing up your one drive onto your one drive, which is pointless.