I would file Married Filing Joint for 2013 and include all the income information you have.  If there is omitted income (wife's Jan W-2 income) then the IRS will adjust the return if necessary.  This way he gets the standard deduction for a married couple rather than for a single person. Then 2014 forward, unless he has children and qualifies as a Qualified Widower, we would file single.

Since the IRS requires a separate release Form 8821 for husband and spouse, to get her transcripts you would probably have to have a court document assigning him as the executor of her estate, or something similar, in order for him to get his wife's transcripts.

I would have him sign a Form 8821 Authorization to Release Information for 2013 forward (I actually use 2000 for all releases) then use www.canopytax.com free transcript interface to pull transcripts for all year and all forms (income, returns, account, etc) for him.

Theban Tonnesen, EA, LTC