OK, the reason you're getting the prompt for every record is that you have omitted the closing double-quotes before the \o switch in your FILLIN field. Hence the switch doesn't work. You have:
{ SKIPIF{ MERGEFIELD Job } <> {FILLIN "What Is The Job Number?\o}}
instead of:
{ SKIPIF{ MERGEFIELD Job } <> {FILLIN "What Is The Job Number?" \o}}

As for the job Nos., the only issue I can see is if they have leading 0s. In that case you should re-code the SKIPIF field as:
{ SKIPIF{ MERGEFIELD Job \# 00000} <> {FILLIN "What Is The Job Number?" \# 00000 \o}}

Note also that your 'Job Number' cell won't get populated unless you have a copy of the Job MERGEFIELD there, outside the SKIPIF field. Personally, I'd prefer to keep the SKIPIF field above the table, too.

__________________
Cheers,
Paul Edstein
[Fmr MS MVP - Word]