Just to add my two cents to your already good projections (the following applies only to 100% urban driving only):

1)- I believe it is not too hard to get 38 mpg out of an HCH-2 - just have to drive it poorly. I find it is a little more difficult to only get 38 mpg out of a Prius-2. In my experience the Prius will do a little better (over 150K urban miles) than the HCH-2. It may not be significant over small distances but definitely a measurable difference over the long run. So, I would adjust the figures to give a little edge to the Prius in your estimates.

2)- An HCH-2 on city duty offers more FE potential than what some of HCH-1 (CVT) owners have stated. Still for an average driver, the HCH-2 offers measurably lower FE potential in the city than the Prius.

Just to give you an idea of what I am talking about: I can get during summer months an FE of 51 mpg on my HCH-2. This is in 100% urban driving. Not too long ago, and under the same driving conditions with my HCH-1 (2004 CVT) I could not get over 45 mpg. Yet, our two company Prius get about the same mileage as my HCH-2. Maybe they would do better if it was not for them being driven by two different people.

However, which ever car you end up choosing, I know you'll be well served.

Cheers;

MSantos