If you're redoing the roof, adding dormers would enhance the look of the house. I wouldn't do it unless I was redoing the roof as you could end up with a leaky roof it something was sealed properly.

Looks like more pictures would help.

The Amish will be replacing our roof as well as fixing the garage area.

Porch will be done like this one I found on Pinterest. I feel our roof needs something. The garage seems like it is taking over (thats a new addition).

I personally believe that dormers are always a great idea, especially for curb appeal :)

they are expensive to put in on a style whim. unless you need the light for living space on your third floor i'd say pass.

The biggest reason I would like them is for our attic we are currently working on, making it a extra bedroom/reading nook.

From the pic, it looks like your second floor windows are not evenly spaced in the wall they are in. If this is true, not just a result of the angle that the pic was taken from, then you want to think carefully about your dormers. A wide shed dormer might be okay, but two evenly spaced dormers would highlight the unevenly spaced windows, if the dormers were over the windows, the roof would look asymmetrical.

you might do better with a shed dormer on the back side then. it gives lots more headroom than just a couple of bumps on the front.

i'm not wildly fond of how shed dormers look (hence the backside suggestion). we have one on our third floor but its up among the tree tops on that side of the house (our gable end faces front) as opposed to being more exposed on the treeless other side.

The windows are not evenly spaced. We plan to fix that when we add new windows before the end of Fall. They have been driving me crazy. I spoke with a professional who actually runs his business across the street. He said if I were to replace the windows evenly, I probably wouldnt want them because it would give me a better look. Which is true, I'm sure if those were fixed, I wouldnt want the dormers for the curb appeal. He did say once the windows are fixed they would look nice and add more height to match our addition and bring both the house and garage together, so it doesnt look like a add on (something like that, he said)....if that makes sense. Once our house is finished (slowly but surely), in and out, I know I'll be satisfied and happy to see our home that sat for many of years prior to us purchasing it...brought back to life and still standing, they wont even matter. Thanks to everyone who shared opinions, it helps to hear the thoughts of others before jumping into a project.