OK reverted back to windows 98 from xp and installed the pinball manager again with 1.5 & 1.6
Under the pinball manager Trouble it says

Unable to update due to fupdate failure [30]

Now because I am on 98 it will tell me details

Beginning Flash update of (Game and Sound) on com1 @115200 baud...|bootdata.rom   0 blocks of 64 (0) sent, total bytes remaining 4980724
fupdate: Pin2000 failed to acknowledge packet (0)

NFI LOL