I REALLY don't like doing things twice ...
This might indicate it is not a DIY project for you. However, if you are willing to do a few bits and pieces twice, you might be able to master the work well enough for a permanent result.
I also hate paying 3-4x more for someone else to do it.
This is often the best motivator, and hopefully provides some perspective. If you end up spending 20% more than a perfectly executed DIY, you are still way ahead.
1, should I do it (hardy) or the cedar
Dunno without seeing it. My house is brick on one face (the north side, oddly) and cedar shingles on the other sides. As long as the finished product looks like it is supposed to be that way, it should be fine. Have you thought about planting shade trees on the south side?
As far as redoing the siding's cladding/sheathing, you probably won't know until after tearing off the siding. It could be that part was well done. I don't think it needs exterior rating because it should be well protected and never in contact with moisture. 1/2 inch plywood or chipboard is standard, but thicker won't hurt and will help a bit with sound insulation and overall durability.
As far as house wrap, brace yourself: it is surprisingly expensive (maybe $100 for one side). If airflow through the wall is a significant factor, like all the other walls are tight and this wall is the big leaker, then it is worth it. If all the other walls and windows leak significantly, then don't bother unless you plan to eventually seal them all.
You might also consider adding additional insulation while that is open, both inside the wall cavity and perhaps as another layer on the outside. This might cost thousands, but given the high price of electricity there and typical air conditioning use, it probably will pay for itself in 8–15 years, as well as being a big improvement in comfort.
If you are going to replace windows, it will be way easier with the siding off than at any other time. The flanges are screwed into the cladding from outside. 14 years isn't all that old of a window, and a straight replacement isn't likely to save much. However, an upgraded replacement could well save on energy costs. Again the pay-for-itself period is probably in the 8–15 year range. Get an energy audit from your local utility (usually free) to learn more.
The pictures you added, were edited with info to help you decide which way you want to go.

There are 3 options to choose
1) Out right replacement of the whole window sash and all.
This is the most expensive way to go about it.
Its benefits are the ability to check the condition of the framing. Windows leak over time and unseen damage will be hidden.
The other considerations are you may need to remove your siding and reset some of it to get you new windows in with their preapplied trim in place. Then again, it is a newer style of window versus sash weights, and the trim or nailing flange will fit very nicely. There is a chance you will need finish it off by covering it with a PVC brick mold.
2) Renovation kit with sash and jamb. These fit a new jamb with sash directly into the existing jamb, saving the existing trim and labor removing the jamb and trim. You only need to remove the sash and track.
- I have seen wood sash versions of this, but I can only find vinyl kits for an example for now.
- This is a cheaper and simpler way to replace windows.
- You really need to make sure the wood that is to remain is not rotted, or has taken on water at any time. This will be your only time to get this in check until you find the rot the hard way, or until the windows are replaced again.
- The outside stop, if all other wood is in good order will need to be covered in metal to keep the wood protected. At that time you may choose to have it all rewrapped to inspect and cover it all without extra seams/joints.
3) Use a jamb reliner kit
- Cheapest of all options
- Needs to meet all of the requirements for option 2
Best Answer
There are replacement window inserts from most major window manufacturers. If your existing window frames are sound, you remove the stops (the vertical strips that hold the sashes in) and the upper and lower sashes. The new window includes a very thin frame with sashes preinserted that attaches and seals to the existing frame. This is done without removing or replacing inside and outside casings (face moldings).
Search replacement window inserts for information from the manufacturers.