Ashley, A contractor who specializes in windows any other exterior applications should be able to provide you with a clearer path from start to finish and most likely better applications and products. Most of the guy/gals that specialize in this really spend the time looking through the products to get the best. Window selections are as personal and vast and any home finishes touch so you will need to decide what you want in terms of look and feel. Once you have figured that out, we can make recommendations inside of a given family of products.

Since you are asking this question, I would get a carpenter or contractor to do this for you.... But here is some info that you need to consider either way. First - Since you are increasing the rough opening (larger header), did you check with an engineer/architect/county inspector that your headers are large enough for load above each window? Secondly - most outer walls are load bearing, and you should support the floor joists for the second floor in front of the each header you are switching out. Also load carried by the temporary header, supports, and their associated jacks need to be resting on something that can take the transferred load. Like a slab on grade foundation, floor joists below, etc. Temporary supports in a basement maybe needed below the temporary support on the first floor to transfer the load from all the way to the foundation just like the load-bearing wall does. Thirdly - Did you get your building permit? If you still have any questions at all about how to do this safely without having your upstairs cast iron tub fall through the floor Get someone else to do this for you. BTW - I will be doing something similar myself this morning, but I am only increasing the header by 4". I used to rough frame houses when going through school, so I have enough knowledge to shoot myself in the foot. I still needed to check with an engineer/inspector to make sure my headers would be larger enough for the load.

You might look at a tilt and turn window unit. That will have a narrower style but still give you access to the porch. It will keep its window lineal profiles but opens like an inswing door.

The windows are Pozzi and still in good condition (other than the seals!). I am guessing that the door is Peachtree because that is what the other doors in the house were. Because the door sizes have changed, the price to replace all the glass is way under what a new custom sized door would be. We have replaced all the other doors in the house and had to have custom doors made. We replaced 2 of them because of issues with replacing locks and handles. The other doors were replaced because they were sliders/french doors that were just not holding up well. This door is seldom used in a walk out basement and still works fine.