Unfortunately, the windows probably should have been addressed before the new siding went on. Doing the windows before putting on new siding would have given you the option of using new construction vinyl double hung with J-channel build into the frames. It also would make repairing or replacing rotted framing members much easier.
However, since you already have the new siding up (would like to see a pic of the window with the new siding in place) you may have to use replacement type windows. If you have rotted frames, those will have to be replaced and the new replacement windows sized to the opening AFTER the frame is fixed. Of course you can carefully calculate the opening based on what you intend to use to reframe the opening, but that can be risky for an amateur. Keep in mind, replacement windows usually have to be ordered to you exact size and are not returnable if you measure them wrong. Always a good move to have supplier measure and order the windows for you. After you install the new replacement windows, you may have to install some new extension jams and exterior trim in order to fit snugly to the new siding. Don't forget to use Ice & Water shield under the finish frame/ over rough opening framing and caulk all areas where water could possibly get in.
Since the original window sash, and not the jamb, were replaced with a window replacement insert, to keep the look the same, you need to do some fabricating.
All this is dependent upon if you can find an exact replacement unit to match the one installed in 2007. The chance of that.... maybe. Window manufactures make changes to their product over time. Your window is possibly not in production anymore, but the next generation of window that carries the same size and some the details is what would now be available. Again, this is only a possibility.
What you will need to buy in addition, and this will be much, much more unlikely, is the wood window unit that matches the original one to the house when it was built in 1991. If you do, you would still need to throw away the operable sashes of that unit and install just the jamb. A big expense just to throw away a major part of it.
If it were me, I would get the materials to make a new wood jamb to match the one installed in 1991.
Construction details for wood window jambs are really quite basic construction. A tablesaw and miter box is all that is needed for tools along with drill and screwgun.
Priming everything before assembly would be essential.
The brick mold on the outside of the window may be the only other part difficult to match exactly. All are basically the same size, but there are minor detailing differences from one supplier to the next. Some folks don't worry over this too much since the differences are so small.
Best Answer
The window had a broken channel balance. I was able to order parts and replace both channel balances. I replaced both since it seemed like I should but maybe I could have just replaced the broken one.
How to replace a non-tilt window channel balance:
https://youtu.be/u4g8Z8jkwTk