Now, that I like…
Ray, I don’t like the skyline on that arrangement. I don’t believe you’d find many examples of a peaked roof butting against a neighboring flat wall. Maybe a sloped false front (shingled) and a flat roof, or turn the roof 90 degrees. On the other building instead of transoms over the second floor windows, how about half that height decorative trim? Editted to Check Steve F.'s post and look at the second floor front.
I can’t explain it but somehow some of the flavor is gone.
Dave
I really like the building on the right, though I’d still like arched windows, at least on the second floor. 
I agree with David about the building on the left. I’m trying to imagine why they’d build it that way. If you want a covered walkway, I’d bring the second story out over the sidewalk.
Hehe! Here I go again! I rather like the setback building on the left. Easy to explain too really. The left building was there first and had a small yard in front. The right building was constructed a bit later right out to the property line. Later still the left “house” was changed from residence to small business and an extension was added in front. Not an uncommon occurance in the real world.
So in a nutshell…I like it! Now, all it needs is an applecart. That’s for you David R.

Troublemaker. 
Richard Smith said:or a wooden indian...................;)
So in a nutshell...I like it! Now, all it needs is an applecart. That's for you David R. ;) :)
Bruce Chandler said::lol:
Troublemaker. ;)
OK seriously.
Many excellent points have been made and I agree with all but especially Dave M. I do like the set back(Richard) on the building to the left but I don’t like the mian roof line for a few reasons. The biggest reason is drainage. You have a peaked roof butting up flat against a brick wall with no slope to the rear. A false facade or front will fix this however in the real world if it poured buckets you would have a swimming pool between the two structures.
I really like the new mock up and feel that your on the right track. What about jib doors on the 2nd floor on the building to the right? They would certainly have been built if someone had the money to make them at the time.
Either that or raise the windows up off porch level.
This is fun as I understand historic architecture and building practices and many excellent points have been made referring to the time period, financial constraints and material availability!

I spent some time today refining the design of the building on the left. I changed the main roof from a peak, to a slope away from the brick building, and added a false front. Also experimented with a mini peak (kind of like a dormer but without a window) on the front of the small sloped roof over the store – makes it more interesting but I’m not sure if I’m happy with it yet.
It sure is nice to be able to work out this stuff in 3D on the computer before building the actual model.
All you need do to retain the peaked roof is to make the building on the left taller than the one on the right. Nice work you do for sure.
Ray Dunakin said:
I spent some time today refining the design of the building on the left. I changed the main roof from a peak, to a slope away from the brick building, and added a false front. Also experimented with a mini peak (kind of like a dormer but without a window) on the front of the small sloped roof over the store -- makes it more interesting but I'm not sure if I'm happy with it yet.It sure is nice to be able to work out this stuff in 3D on the computer before building the actual model.
The computer stuff is way cool. I can’t really plan , I just build but I love to read stuff as such!
One nice thing about what I’m into… I just snap some pics of my prototype and wing it from there. If I change it so what? I know what I’m after when I sit on my deck running my mythical mini NE Corridor and drink beer!
Ray,
How would you have built it before the days of the “High Speed Internet”
Think about that!

Once again you guy’s are the best and make my brain hurt!
I’m generally not big on planning. When I started building in N scale and HO scale as a teen, I would just work from measurements of the prototype. If it was a freelanced structure I would usually make a drawing to get the basic dimensions, and work from that.
Now I mostly just wing it, but for some of the buildings I have such tight space limitations that I need to make sure I can fit what I want into the space, in a way that will look the best. So it helps to be able to knock off at least a crude 3D model. It’s the same as doing a sketch but faster and more accurate.
This is the first time I’ve put so much effort into planning the buildings, even more than when I was designing the (as-yet unbuilt) Dos Manos depot.
Ray Dunakin said:Let's just blame Dave Marconi for you spending to much time on planning! ;)
This is the first time I've put so much effort into planning the buildings, even more than when I was designing the (as-yet unbuilt) Dos Manos depot.
I made one more 3D mockup:
(http://www.raydunakin.com/IRRWebfiles/wIMG_3880e.jpg)
As you can see I made a few modifications to the building on the left. I also changed the building on the right from brick to stone, and went back to arched windows for the second floor. As before, this image still doesn’t have every detail in place, but it’s close enough now that I’ve finally started work on the actual models. I’m building the left structure first. I began by building up the shops from styrene strips:
(http://www.raydunakin.com/IRRWebfiles/wIMG_3909.jpg)
(http://www.raydunakin.com/IRRWebfiles/wIMG_3916.jpg)
(http://www.raydunakin.com/IRRWebfiles/wIMG_3923.jpg)
(http://www.raydunakin.com/IRRWebfiles/wIMG_3930.jpg)
(http://www.raydunakin.com/IRRWebfiles/wIMG_3942.jpg)
(http://www.raydunakin.com/IRRWebfiles/wIMG_3945.jpg)
I’ve finished the windows that go on either side of the door. Next, I’ll make the door and join the three assemblies together.
Great start Ray. A fine looking group of structures.Beatiful detail on the build. This road is definitely a showcase.
Great looking windows!
The new design looks good, Ray.
David is right. The block will indeed be a showcase.
Ralph
Wow!!! What the 3 of them said… Fantastic… 
Very nice Ray 
Thats going to fit into your RR very nicely.