Measuring for a replacement window is totaly different then measuring for a new construction window.
Your measuring the inside of the jams, the sill and head piece distance, not the R/O of the framing.
Once you get those measurements you subtract 1/4" and that's the size that needs to be ordered.
Replacement window can be ordered to the exact size you order, there is no 2" rule.
There is no need to take anything off to just measure the opening.
In most cases it takes about 2 weeks to recieve the new windows.
There also going to need to know what type, placement and number of lights (fake window panes) you want.
EG: just because your old windows may be the common what's called 6 over 6 does not mean you have to stick with that, in my case I choose them to be 3 over 0, that way there are no deviders at the bottom restricting the view.
If your's the type I'm thinking of the sashes are held in place with window stop that will need to be removed with a flat bar, then you raise both sashes and pry out the metal tracks just enough to get the staples to pull out of the jamb. lower both sashes and pop out the top ones.
You should now be able to grab both sashes and give them a yank and the whole thing will come out, tracks and all.
Your going to need about 3/4 of a tube of caulking per window, make sure it's paintable caulking so it can be used inside.
Your also going to need some low expanding foam, it's used to fill any gaps, I also use it to partly fill in the huge gap at the bottom of the window before installing the outside filler strip.
Once you get past the first one you should be able to remove and install a new window in under an hour.