I think at this point it's best to see it as 2 options.
a). The movie begins in May 2008 and it takes Ivan until November 2009 to complete his armor.
b). Vanko and his father aren't watching "I Am Iron Man" live and the movie begins in November 2009. Given his father's hatred for Howard and most likely Tony, it makes sense he would have recorded the speech and hate watch it. Ivan telling him to turn it off could be because it's a continuing thing his father does.
We see a number of news articles and magazine covers that show time passage in the opening montage. Whether it's the montage itself or they were already there pre-montage, I think it's easy to see how Ivan can't finish his armor in May 2008.
I think it's a good compromise with all the evidence. The main contradiction to this is Fury's "last year" comment when referring to the events of Thor. 2010 fits with Natasha's "over a year without an incident " line with Bruce, fits with the 2010 Stark Expo promo, fits with the Monaco Grand Prix falling in May 2010, brings Iron Man 2 around its release date, Thor around its filming date, and The Incredible Hulk closer to its release date, and it allows more time for Tony to turn the Metlife Building into Stark Tower.
One issue I have though is how the week in What-If is shown. The nexus event in What-If shouldn't affect that portion of the timeline and it should match with the MCU. That episode begins with Tony at Randy's Donuts on a Monday which would mean it's May 31st, 2010. This is meant to be the day after his birthday party with his birthday falling on May 29th. I guess we could assume that while his birthday was the 29th, he didn't have the party until the 30th, but 2011 would have fit these days perfectly.