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Looking for Software with this feature

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Curt:
take a look at RichCopy-MilesAhead (June 30, 2015, 09:33 AM)
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RichCopy has not been updated for 6 years, but other than looking old, it is really fine  :up:
Look for "Joshua Hoffman Code download available at: HoffmanUtilitySpotlight2009_04.exe (5,896 KB)"

MilesAhead:
This link has a description of the features for RichCopy

RichCopy Tutorial

4wd:
I don't think either Robocopy or RichCopy are going to help with item number 2 in the OP because neither of them can rename on file collision.

ie. 'move' and 'keep both' implies one of them needs to be renamed.

See here for an example of using Robocopy and renaming a file:
http://stackoverflow.com/questions/21034925/robocopy-file-structure-rename-file-at-destination-if-its-newer

Should be reasonably easy to modify one of command files I've done to cater for both conditions.

Basically, the one from here with tests for name and size, (minus the shortcut stuff):
https://www.donationcoder.com/forum/index.php?topic=40412.msg377497#msg377497

But then you're talking about the ability to create filters which goes beyond a simple command file and more into the realm of a backup/sync program with multiple conditions/results.  Something similar was asked for recently and I don't think anyone came up with program that fulfilled the requirements.

MilesAhead:
In the Other options in the help it says there can be a command to run before the copy starts.  I don't see where to specify it.  But since it is a move you could conceivably scan looking for collisions and do a rename on the target end and do the move.  Once those are all out of the way, assuming we figure out how to do the command, the regular copy process commences.  Since the source has already been deleted the collision should not recur.

ednja:
Here is an example of moving a file of same name into a folder that already has a file with the same name, but the two files have a different size.  Windows 7 already determined that they have different sizes.  This is the reason why I believe it should be possible for a programmer to create a program with such a filter.

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