Do you have an overhang on the front?

It appears that the second story window in the photo above may conflict with an overhang there?

I thought a few more points. To extend the roof off the back of one foot the city inspector where they said the contractors should put in sister joists at least 2 ft back so they will have to cut open the decking to put those in. Someone from CertainTeed suggested they also put blocks of wood to support the sister joists for added stability.

An overhang is not a good idea in snowy climates. Ice dams form on the overhang and melt water from the ever so slightly warmer roof above backs up and gets under the shingles.

Thanks a lot for mentioning that. I live in Michigan so definitely get snow.

Thanks for the additional comments and read up about the benefits of proper venting long with ice and water shield. Also thanks for the comment about the window possibly interfering. I didn't realize how close it was to the roofline. Would the interference come from the extended roof intruding into the window frame?

It should be no added cost to put in a continuous peak vent if you don't have one. You can increase the size of your 3 gable vents inexpensively. That's all I'd do for this house. There are thermostatically controlled power roof vents for episodes where conditions warrant more flow. You could add one of those to each roof segment.

Thanks for the tip about the continuous peak vent and is that the same as a ridge vent? Also wanted to ask about increasing the size of the gable vents, because the contractor came out wants to close off the gable vents and install bbetter soffit vents to get the air flowing from bottom of the roofline to top of the roof line.

Same as a ridge vent. The gable vents will work fine because hot air rises. And the savings in money will be very substantial.