Here is a sketch noting the boiler vent that isn't seen in the picture. We are fine with all the plants being moved, etc. so sky is the limit on suggests!

You don't have enough vertical space to mount a flat roof, even, so you would have to build a gable atop the existing hyphen roof with sufficient projection to create the desired portico depth. I guess it could be a hip roof too.
Casey

I would think about curves rather than straight lines. Let how the people walk toward the house determine where the walkways should be so it's more organic. Make the step a little wider and put some white railings on either side to highlight the entry. Maybe add a metal decorative piece of art on the chimney.

Casey - I'd love to have a great looking portico but I know that's out of the question with the roof lines. Now we're focusing on figuring out what to do with the decking portion.

Annie - Thanks for reminding me about how people actual approach the house! The steps that you see are wooden temporary.

The main debate in the house is do we just added wider steps with rails (similar to what is already there, just wider), or a front porch/deck that spans the space with room for a chair or bench (like the attached picture...but even that's not quite it)

Thanks!!!

I would prefer just the steps and then you can make a much larger area all on one level with the garden which you can expand or shrink as need be. If you try to fit in a porch it will be small and constrained. Plus your house style doesn't really encourage a porch.

Will you use the space as a sitting area? Or do you have other space in the back and this will be just an entry area? And since this was a breezeway, I'm assuming the front door is someplace else and this will be more of a family/service entrance....

Annie - I'm having difficulty imaging what you mean by "a much larger area all on one level with the garden..."

This is the new front door. If it were more of a porch rather than entry steps we would have a chair like in the picture above.

Thanks again!

I think ther is some potential for adding a portico on the from, just have to be correct in scale. I think that is what I'd like as it provides some shelter from the elements when staining in front of the door.

Here are some examples:

See mclarkes post here http://ths.gardenweb.com/forums/load/decor/msg03131830794.html

Or here
http://www.city-data.com/forum/kansas-city/929088-building-portico.html

The inspiration pic you posted is a porch with a roof, but I don't see that you have enough headroom for a roof. So you'd be looking at some sort of deck type area, but then you would be limited to putting chairs only on the deck area...probably so narrow that you could only have the chairs face out, as in your picture. Or as in this one with a pergola.

If instead you build just steps to the front door, then you can build a patio at ground level which could include a seating area large enough for people to gather perhaps putting a fire pit in the middle.

Or if you don't want to use the area for seating, you can still dress it up with plantings or a fountain.

Annie - Now I see what you're saying :) We are thinking more of a decorative bench, chair, etc., not an actual seating or gathering area. Sorry, I should have clarified that better. If we can't do a true roof (which from what I'm gathering is going to be difficult) I do like the look of the pergola. Honestly my inspiration is a portico but I've been told that it isn't possible with the roof line...maybe I need further opinions.

Lyfia - I'd love to have a portico for just what you mentioned, cover from the elements. Thanks for the links.

In my mind I see two main options:
1) a deck/porch that spans the entire space (from the left side of the chimney to the brick in front of the car). But I can't envision how the walk would like, the steps, etc. and if that's just too overwhelming.

2) Steps to the door with a possible portico with a curved walk to the drive.

I wish I was handy with sketch up, etc. to envision.