$ cat myscript.awk

BEGIN { OFS="\",\"" }

FNR==1 {        for(X in A) delete A[X];        }

match($0, /:/) {
        N=substr($0, 1, RSTART-1);
        V=substr($0, RSTART+2);
        sub(/ *$/, "", N);
        A[N]=V;
}

/^Original Path/ {
        print "\"" A["Custodian"], A["Export Path"], A["Matched File"], A["File Size"], A["Original Path"] "\""
}

$ awk -f myscript.awk datafile datafile datafile

"Jim_Foo-HDD1-FOO-1234","N:\FOO-1234\Foo_Foo","foo_file1.pdf","640","foopath\foopath\foopath\foobar\foo_file.pdf"
"Jim_Foo-HDD1-FOO-1234","N:\FOO-1234\Foo_Foo","foo_file2.pdf","123","foopath\foopath\foopath\foobar\foo_file.pdf"
"Jim_Foo-HDD1-FOO-1234","N:\FOO-1234\Foo_Foo","foo_file1.pdf","640","foopath\foopath\foopath\foobar\foo_file.pdf"
"Jim_Foo-HDD1-FOO-1234","N:\FOO-1234\Foo_Foo","foo_file2.pdf","123","foopath\foopath\foopath\foobar\foo_file.pdf"
"Jim_Foo-HDD1-FOO-1234","N:\FOO-1234\Foo_Foo","foo_file1.pdf","640","foopath\foopath\foopath\foobar\foo_file.pdf"
"Jim_Foo-HDD1-FOO-1234","N:\FOO-1234\Foo_Foo","foo_file2.pdf","123","foopath\foopath\foopath\foobar\foo_file.pdf"

$