Which windows work with which automated window openers

Honestly, letting your wife pick what looks best is the answer. The double tilt sliders are nice if you want to pop them out and clean them I guess. I like the awning ones because you have a bigger window area without sashes in the way. If you do get the awning style, make sure the crank mechanisms are replaceable. I have one in my bathroom that basically isn't repairable without taking the whole thing out. Whether you will actually be opening and closing them and how much airflow you want to have is another consideration. You may not want to have to crank it in an out or remove the screen to unlock it.

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.