I don't know Jason, so I'm just going to reiterate what I think you are trying to do, and give you an answer for that assumption.
Do you just need the last 5? If so, you don't need a regex.
For each %CurrentItem% in files
Get subtext from %CurrentItem.NameWithoutExtension% starting from %CurrentItem.NameWithoutExtension.Length - 5% to end of text
Then for Rename Files, looking at your loop, the If statement (steps 8-11) would rename the %CurrentItem% and then following that step 12 would try to rename the item again, but if %CurrentItem% has already been renamed, then you aren't going to find %CurrentItem% where it used to be, so step 12 will always error out if the if statement is true.
If you are trying to use one rename or the other, you want to use IF -> Else. It goes like this:
If (calculation is true)
'do something
Else (if not true)
'do the other thing
End (if)
Also, %Match% is just 5 digits, correct? If so, you can't use Match for the If file exists parameter. It needs to be a whole file path: something like %FromPath%\%Match%.jpg
Hope this all helps.
