From the photo - That is not black trim. That is the storm window frame with a black accent paint around it. I can guarantee you that when you remove the storm window, the fin of the aluminum window beneath it will not be exposed. With vinyl siding, it is NEVER correct to install exterior trim on top of the siding. I don't know what your original siding was, underneath the vinyl. Do you? But with aluminum windows, I can almost guarantee you that the siding butts up against the window frame. IF there was a casing trim of some kind, it was most likely removed when the vinyl siding was installed. You remove the storm window. Then you remove the sashes/glass and mullions (if any) from the window, leaving just the frame. Then you pry the frame into the opening, pulling out the nails. You also hope at this point that the vinyl "J" channel was not nailed through the window fin. If so, the "J" will come off with it. When the frame is out, you then have the opening you will be dealing with. You can have the new window made to slip between the "J" and cutting back the sheetrock, or you can have the new window made to fit sheetrock to sheet rock, and trim the outside appropriately. You'll be able to see where the studs are, and the window cannot be bigger than the rough stud to stud opening. The problem is the vinyl siding. I hesitate to recommend cutting that back. Perhaps someone else here has a suggestion on how to do that without risking cracking/chipping and ruining the siding. The other problem with cutting it back to reveal the window fin is that you no longer have the right "J" channel - though maybe they can find some and slip it around the siding cut. But then you also cannot nail it properly after the fact. This is why I recommend leaving the "J" and siding alone. What abosolutely MUST be done in your situation is that the proper drip cap/flashing MUST be applied above the window. It must go up behind the sheathing, and turn out over the window, extending past the "J" channel, and then a downward bend of app 1/2". In your case, you have to have someone custom bend that on site. The addition of vinyl siding will make any pre-made drip cap unusable. It must start from up behind the sheathing or original siding, NOT the vinyl siding. Also make sure that the new windows are fully injected around the frame with low expanding insulating foam. This will be an absolute must for your application. That's probably clear as mud. But I did my best for you. Keep in mind, this is a standard every day job for any competent window company, and I did thousands of windows like this that never leaked. But if you get a crew in there that takes short cuts and depends on caulking for shedding water, you're going to be in big trouble down the road. Hope that answers your question. What the other guys here said is more true than you can know. "Contractor" guys are clueless about this kind of stuff, and it shows in the end results, and we've seen it a million times. I also want to tell you that if you chince on this, you will get a chince result and look. The money has to come out of somewhere. You don't want it to be the product or the workmanship. Pay for a good job done right, and you won't be doing it again in less than 10 years. Ignore this advice, and you will. It's not an insult to your intelligence, which I'm sure is adequate. It's just the fact of it. And unless you do this for a living for years, you cannot know, and I don't mean to offend, but that's the reality.

Ok here are some pictures. Its the second floor so I used the zoom. Hope you can see well enought. Finished exterior: http://oi41.tinypic.com/k2mwt2.jpg Zoomed in: http://oi44.tinypic.com/2d8f8dj.jpg The bottom zoomed in (not sure if he caulked that actually): http://oi41.tinypic.com/29urgx3.jpg For reference, here is the downstairs bathroom window which has not been replaced yet: http://oi43.tinypic.com/309o8bn.jpg From bottom: http://oi41.tinypic.com/ogvz3o.jpg The side ( ignore the tape from party favors) http://oi43.tinypic.com/296oqxx.jpg For reference, this is the bottom of another window I am planning to replace. Not a bathroom window but its similar trimming. http://oi44.tinypic.com/avr7rd.jpg

All righty then! Excellent work - period, end of sentence! Hope youll post back to show us the "after". Re scaffolding, may I piggy back ont his thread to ask - how much of an ordeal is it erecting and moving it? I have a 1 1/2 story and am trying to decide whether to attempt scaffolding or get/borrow a taller extension ladder.. I think the ladder might be a lot of hassle having to move it so much and futz with it each time.

The area that frames the garage door. It is usually made of wood. And painted every so often to keep it from rotting. In Canada, ( other places also, Im sure) some contractors recommend wrapping this area in aluminum to keep the elements out. Similar to what they would do on a window retrofit. If you have ever seen this done, Let me know what you think about how it looks. Would just painted wood look better?