If you are putting up new siding, going a full tear out with a nailing flange is certainly an option and preferable if you can afford the added expense of new interior trim, stools, etc. That will get you back some of the glass lost in a typical pocket or insert style replacement and give you the most complete type of installation (assuming your contractor is competent). Look for a window with an integrated J-channel and nailing flange.

What a lovely home. I really like the vintage aluminum awnings and was considering putting a modern version of them on my 1940s home (but we are now selling it). There are several neat options on this site. http://www.generalawnings.com/aluminum-awnings-c-65?sort=20a&page=1 I like this stripe design, and it's available in a number of colors. http://www.generalawnings.com/aluminum-awnings-c-65/3100-series-window-awning-p-199

If you make the other changes as suggested, I don't think you'll feel the need to paint the brick. There's no sense creating a maintenance issue where there is none now. The house has the potential to be very handsome. Some pretty pots with flowers on either side of your door will add some color as well. Don't forget that nothing looks pretty this time of year when trees are bare and lawns are brown.

Thank you, all! HAHA, Denita..I've never cared for those garage windows. We are replacing the garage door. I definitely like the clean lines of the windows above....thank you, Phuninthesun! I was hoping you would play with these pics! Is there a tool I can download to do the same? I love the denim color, just not in that spot. I really like arctic white vertical board and batten for the gables....we are contemplating metal sheeting on the right side..... your pic, Housegal200, seems to resemble the style of new homes in the neighborhood...I like it. Yes - we are dramatically renovating the exterior - the wood is termite damaged and literally falling apart in certain areas. We'll install Marvin windows and French doors; black has become popular on farmhouse style homes at the beach-i hope its not too trendy-i like them. here's a mock version we are thinking about but with a garage door that has windows LOVE this Hardie ARTISAN Series siding - - perhaps installed along both sides of the house?