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I am working on a house with very similar situation. It was built in 1950, when I got it, it has leaks, vinyl siding over asbestos siding, 3 layers of drywall, zero flashing so all windows leak, it was held with only a few studs while others were all rotted. I tore everything up, sidings, drywalls, floorings and replaced all damaged wood. Now I am about to work on the roof. My roof has same structure as yours and has same sagging issue. I am in between of sistering and replacing all the rafters. What will you do?

Need to do your floors first without solid floors you don't have a solid foundation without a solid foundation you don't have anything to build off of

MAybe relocate the carport or a garage on the left side if you move the kitchen to the front left side and have a door from that side go straight into the new kitchen.

Now that I look at the bluepring more, you'll likely need to make that room on the right (the addition) larger. Bump the back wall out to line up with the back wall of the current dining area. Make a master suite out of that room with a private bath in it. Don't have an exterior door in the master suite. Make a separate garage or carport in a different area and let everyone use the front door or the back door off the kitchen.

Retired contractor here. Done hundreds of these, small and large. There's plenty to do here and depending on where this is located costs could vary widely even with you doing a lot of the labor. Not just fixing it to sell quickly works in your favor. Address the foundation and beams first, then level floors, then the roof. Tear off the metal carport and extend that addition to the far edge of the carport and make the roof on the extension match the existing one to better control rain runoff. Create a barrier to keep vehicles off the septic and drainfield area, no planting garden there - roots might clog the drainfield. Tear off the back porch and either rebuild or do as you want (open deck/porch). That front porch design looks nice if it fits with all other plans. You might remove the center bedroom on the left and make a bath there and some closets in that space to give the remaining 2 bedrooms more space. As a possible alternative, tear out the inner walls. Move the kitchen to the front left with the dining room integrated with it in the area of the front and center left side bedrooms . Leave the third left side bedroom there, On the right back put a bedroom where the current kitchen is and a bath where the current dining area is with the new living area in the front right. Then a short hall to the addition bedroom on the right. In that addition on the right, move the bath there to the left side and the rest is the bedroom. Once you rip out the existing carport and extend the roof of the addition, you can still park under the new roof and maybe build some outside storage into that as well. It's going to be interesting watching all this happen no matter which choices you ultimately make.

As a guy who has renovated several old houses, I will offer the following suggestions. First of all, respect what the house is. It is a nice vintage house and I urge you to avoid getting carried away trying to change it. 1. Regarding the roof, my feeling is that this should happen relatively early. However, if you are planning on leveling the floors, that should happen first because doing so can cause leaks in sound roofs. A standing seam metal roof would be appropriate to an old farmhouse but there is nothing wrong with shingles. Pesonally, if you choose shingls, I would choose a neutral color mix, say black and dark grey. In my opinion, trying to get the roof level is not worth doing unless your roof rafters are compromized. More likely, they are sixty years old pine and as hard a rocks. If you try installing bracing, that will transfer the loads to your ceilings, potentially causing problems with them . I say re-roof with well made and designed flashings and be done with it. 2. I urge you not to muddle with the rafters, or make changes to the roof archtecture or look. The exposed rafters tails are part of the look. They have lasted this long. Keep them painted to prevent rot. Gutters cause their own probelsm. I say "no." When you re-roof, let the roofing and flashing extend slightly (1/2 inch) past the roof decking so the water falls off easily without soaking the decking or rafter tails.Maintain it an leave it. 3. The house has really nice four-over-one windows. I would want to keep them, perhaps adding external, removable storm windows for energy efficiency but first, I would see to it that they are painted and that their seals are inact. They are an asset to the house, especially compare to cheapvinyl windows. Again, maintain them and lave them. 4. A fireplace with a working chimney is an asset to the house so long as the fireplace is in a reasonably good location and is structurally sound. If you don't have a damper, get one. Maintain it and leave it. 5.You did not talk about the floors but if you have original wood floors, they too are an asset, even if imperfect. Refinish them and seal with an oil finish. 6. Please, please, please, don't go removing the period millwork and walls in order to "modernize the house." That stuff is part of the character of the house and is almost irreplaceable. Exceptions to this are, possibly" the kitchen and bathrooms(s). However, save any millwork you remove in order to make your remodeling seamless. Okay, now I have saved you a bunch of work and money and, hopefully, another great vintage home.

I think adding a bathroom is a good move for the house. You might be able to increase the closet space in the other two bedroom as well.