Greetings,
I am in the early process of educating myself about window installation, and I have an incredibly 'newb' question for you pro's.

In this property (pic): http://www.gfxmoo.com/front/homestead_10.jpg

You can see the very small front windows. I am planning on replacing them with a set of 2x4 double hungs around a 4x4 fixed.

I am familiar with the process from the interior prep, framing the opening and installing the 'window'. However, with regard to flashing it properly from the outside.....how is that best approached in this situation?
Obviously that wood siding must come off to allow for flashing?...(gulp)....but how to do it without destroying the siding?

Bottom line: How to approach the exterior work on this without tearing apart the whole front of the house?

Thanks for any insight!
(btw - I am going to hire someone to do 1 window set,....and then hopefully I can do subsequent windows,...I am aware this is not a simple DIY job for the novice like myself).

 

In order to get the siding off, you reverse the order it was put on. Since it was installed from the deck up to the ceiling, you start as follows:

Take off the shutters, take off any trim where the siding meets the ceiling, take off the siding to one couse below the bottom of your new windows.

Yes you will have to basically take off all of the siding if you are going to install new windows with mounting flanges and you want to flash the windows.

Your going to have to cut the siding to fit back in anyway as you window openings will be much bigger, so removing it is not going to be that big of a deal. Just get some thin pry bars and tap the bar up under the edge near where it is nailed and gently pry up to avoid splitting the siding. You'll have to work your way along the length of each piece, prying at each nailing point until the board comes loose.