Not sure where this is located but the number for Sears Pension Plan is 1-800-953-5390. Medical benefits 1-877-254-6765
Not if you mean drawing the form yourself on a sheet of blank paper. If you mean finding the digital form online and printing it yourself at your own computer, that is fine (the site to find them on is irs.gov).
You can also use tax software to do your taxes and answer online questions instead of filling out the form yourself, and the taxes can be submitted digitally if you used an approved software.
They payee. You will receive this in the mail so you can file it with your income taxes.
The W-4 is used by your employer to withhold the correct federal tax from your income. You must fill it out and return it to your employer.