Any thing is possible if you have the money. Maybe your assartion "can't be that hard" plays a larger role in noone wanting the job. No i have never done what you perpose simply because what you have now alows better ventilation.

Money talks. Any customer who devalues skilled labor though, generally doesn't have money that shouts enough to have someone deal with taking the job.

I think they look way better when done like this: eave return. It's really not that hard, I'm not sure why you think that assertion demeans or devalues the labor involved. It takes longer and costs more, which is why it's not done on a lot of new construction, but should not be beyond the skill of anyone who bills themselves as a professional carpenter. I've done them that way myself and I'm sure as heck not a competent pro. Doing them as a retrofit will certainly not be a trivial job in terms of time.

When I said it can't be that hard, I meant that it to a layman like me it looks like a trim job, but maybe it is more complicated than that. Since I am not a professional, I don't know if it is complicated or not. That is why I am asking the question. And rather than speaking to 50 people on the phone or making appointments and wasting everyone's time, I am asking the group that seems to know everything about everything when it comes to building and design.

I have talked with contractors and asked for quotes, but I get no response or say it can't be done. Why can't it be done? Is it because the entire dormer has to come off the house? Is it because there would be leakage problems if we mess with what is already there? Is it because the people I talk to are not familiar with classic or traditional architecture or aren't skilled enough to know how to do anything but the "pork chop" style? Could it be that the risk is not worth the return? Should I talk to an architect or could a contractor that does wood working do the job, or is there someone else I should talk to? Is this a $500 job or a $50,000 job?

I guess I would like to know more so that I can be more educated and find the right person for the job. That's all.

In the pictures I posted, it appears that the "box" for ventilation is still there, but in the after picture there is no trim on the front (the part that looks like a pork chop). It looks like you take off the front and re-work the trim. But, again, I am not a professional and I could be totally wrong.

Thank you rwiegand for your comment!

I think "dormer" may be the key word. One dormer is such a small job, by the time the contractor sends out a 40 ft ladder and two guys for a day you have spent a grand. If it needs a man-lift, then even more cost. He probably thinks that is not going to be worth it to you, so why bother with making up an estimate for a job that's going to stay in the ether? When you call, make sure he knows you are very serious and money is not an issue.
Depending on what it looks like once the returns are taken off, it could require re-trimming most of the front of the dormer. That means unless you begin with that assumption, it is a prolonged job. Depending on the siding material, there may be more complications; stucco does not like to be disturbed; taking down all the trim that surrounds it (or Hardi siding) will raise more issues.
Yes, water-shedding detailing of dormer trim is very important, they often get short shrift in the scheduled maintenance department.
Casey

I think Casey's estimate is probably pretty good. It will involve taking apart the existing corner, perhaps the siding as well, adding or correcting the framing underneath then building back the structure, flashing it correctly, fixing the disturbed siding, and re-painting. None of this is "hard", but it is fussy and time-consuming. Around here I can't imagine it would cost under a kilobuck for each corner done, perhaps significantly more. Most of us would choose to live with an ugly pork chop instead, and the contractors you've spoken to may well assume that. Perhaps you need to open the conversation with "I know it's crazy and will be absurdly expensive, but..." If it's the one detail that will transform a facade to something really charming it could well be worth it to you.

It would help to see a picture of your actual dormer.I would be glad to explain what is involved.It can be done but there are two ways that I could do it and a pic would help to get my explanation correct for your house.

betsy031799:

I'm inclined to agree with klem1. I suggest you tell a contractor you will pay for his time to come out and explain the cost effectiveness of the alternatives. You'll be out 3-500.00, but you'd have your answer. This is an excellent qualifier for the contractor. A customer that doesn't have a problem with a paying for an estimate is most likely serious.

I just emailed a similar proposal this morning. Of course, I've heard nothing back. Better to be out an email than several hours of driving and meeting for nothing. Worse yet, providing professional information for free and getting Craigslisted by the homeowner.

Thank you all for your responses, this has been very helpful. I am attaching pictures for you.

There are four dormers. Also, ignore the uneven return over the bay. That is a separate issue entirely!

I can understand why he contractors told you it could not be done after seeing the actual pictures of the dormers.It can be done but would be very involved and I don't see how the price to do it would justify it.I think the way it is done now adds a lot of detail and looks good to me. If the eaves on the dormers had more overhang and lined up with the rake on the gable better it would not be that complicated but it is what it is.I can explain what would have to be done if you are really interest in having it done.

Imagine a straight line coming down from the rake of the gable end fly rafter.It would be quite a bit lower than the fascia on the eaves .This is where the problem is and what makes it complicated and expensive.