Get-Content file.txt -replace '"\$"', '' -replace '"', '' -replace '(.+)', '"$"$1"$"' | Out-File file2.txt
There are no real pros or cons compared to -replace '("\$"[\w\s]*)(")?([\w\s]+(Get-Content D:\Programs\actual\Folder3\Output\SolidFile.csv) -replace '"\$"', '' -replace '"', '' -replace '(.+)', '"$"$1"$"' | Out-File D:\Programs\actual\Folder3\Output\SolidFile.csv
Also, be careful, you are overwriting the original file. Dangerous if in a pipe, which reads the file content while it processes (and replaces) it - leading to an empty output file ... The parens take care of that, as file content is first read in completely before getting processed.
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It is matching your specific example patterns though. EG:"$"Limited Company "Maxis Segar ""$"
"$"Limited Company Maxis Segar "$"
"$"Blah Blah "$"
"$"sdfsdfsdf "Blah Blah" "$"