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These are the Folders and Disk space being occupied by the Data held on by Apple iTunes as laid out below:

I have written down some current thoughts & steps/ direction as well for each. There are lots of duplicates in the Backups & VoiceMemos (determined via a Duplicate File Finder).

Please help / guide me in organizing and doing a comprehensive clean out of things in these folders.

Items in Italics represent key questions on how to go about a certain part of this process?

Here is the Folder Tree, Space they occupy and Observations & Thoughts.

C:\Users\Alex\AppData\Roaming\Apple Computer

..\Logs\CrashReporter – 300 M

C:\Users\Alex\AppData\Roaming\Apple Computer\MobileSync

..\Backups – 24.5 GB

Clean iPhone 4 Backup

How to Eliminate Duplicates in iphone 5 Backup? (Search Again)

Migrate?? iPad Backup? (What Size is it?)

C:\Users\Alex\Music\iTunes – 39 GB

Cache – 327 MB How to clear?

iTunes Media – 28 GB

Mobile Applications – 26 GB

Voice Memos – 1.3 GB

.m4a files: 20100618 – 20150319 (Maybe some overlaps??)

Downloads – 700 M

.TMP Downloads - DELETE

iTunes Music – 10.8 GB

Podcasts – 5.9 GB - >> Migrate / Export? How?

Mobile Applications – 4.4 GBHow to consolidate to single MA folder?

Older Applications – TaiChi – Economist World in 2012

How to check if any/ which apps are being USED or SYNCHED?

Some are being used.. and Synched

Others are ancient.. Eliminate/ Migrateable

Maybe Migrate all and then Sync back from Phone.. See what remains?

Voice Memos – 240 M - How? Consolidate to Single VM folder

.m4a files: 1/26/2011, 19040101, 20100703 – 20120506

Music – 100 M

Yoga/ Rave – (Poor titling and Tagging) – 45.6 M – Check & Delete

Few Singles – 50 M – Migrate and Clear

Books – 68.9 M – ePubs

Downloads - .TMP - DELETE

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Safe to do this…

C:\Users\Alex\AppData\Roaming\Apple Computer

..\Logs\CrashReporter – 300 M

Delete contents of - \Logs & \CrashReporter but to be on the safe side, preserve the folder hierarchy, just in case it wouldn't auto-recreate if needed.

C:\Users\Alex\AppData\Roaming\Apple Computer\MobileSync

..\Backups – 24.5 GB

Make a new one, delete all older.

Clean iPhone 4 Backup

How to Eliminate Duplicates in iphone 5 Backup? (Search Again)

Migrate?? iPad Backup? (What Size is it?)

not sure about this section, could you clarify in your question & I'll change this answer

C:\Users\Alex\Music\iTunes – 39 GB

Cache – 327 MB How to clear?

iTunes Media – 28 GB

Mobile Applications – 26 GB

You can actually clear all mobile apps from here if you really need to save space. They're all purchased & can be re-downloaded if needed.

Voice Memos – 1.3 GB

.m4a files: 20100618 – 20150319 (Maybe some overlaps??)

These you would have to chase manually.
You'd have to find an app that will play them without duplicating to another location, which iTunes would do by default. [unless they already show in iTunes, in which case you can audition from there & delete as necessary.]

Downloads – 700 M

.TMP Downloads - DELETE

Always safe to delete temp files.

iTunes Music – 10.8 GB

Podcasts – 5.9 GB - >> Migrate / Export? How?

Migrate by simply copying to another location.
I'm not fully familiar with how iTunes deals with podcasts it thinks it ought to have but can't find. Might need to experiment.

Mobile Applications – 4.4 GBHow to consolidate to single MA folder?

I wouldn't try to move apps, as you might just end up with duplicates. I'd either leave, or if space is at an absolute premium, delete.

Voice Memos – 240 M - How? Consolidate to Single VM folder

Manually, as above.

.m4a files: 1/26/2011, 19040101, 20100703 – 20120506

Music – 100 M

Yoga/ Rave – (Poor titling and Tagging) – 45.6 M – Check & Delete

Few Singles – 50 M – Migrate and Clear

All music would need to be handled manually, from within iTunes.
The exception would be anything you already threw out of iTunes, but didn't tell it to Trash - those would be an afternoon of guesswork & comparison, I'm afraid.

Books – 68.9 M – ePubs

Again, manually, as music above

Downloads - .TMP - DELETE

Delete.

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