First the things that make HOLES, then the things that FIX holes, then the things that make it pretty.

1 - Water issues ... Roof and any leaks around windows or porches. Because unless you have a dry house, nothing else matters. Drainage if it affects the house.

Have vent pipes installed when you have the roof done.

Chimney repairs might go here
2 -Plumbing and electrical upgrades ( they make holes)

3 - Replaster ... after you have done plumbing and wiring and any molding removal or window changes.

INSULATION: only after you are SURE you are through with
the attic for wiring and plumbing and vents. they chareg extra if they
have to deal with insulation.
You can get CHEAP energy saving
by that plastic window film. Looks ugly as sin, but it saves money and
makes you more comfortable.

When you say "walls" what's wrong with them?

What is the problem with the basement?

What is the problem with the steps?

What is the problem with the chimney?

What is the problem with the driveway? (I'd put it very low on the list)

What is the problem with the kitchen?

What is the problem with the flooring?

More Pictures would help.

My thoughts here are that you have a long road ahead of you - so if you are overwhelmed before even starting on a massive old home reno perhaps step back and ask yourself if this is a journey you should even take? Consider instead the alternate: downsizing to a smaller home that doesn't daunt you as this one does. I'm not a therapist, but I sense a level of anxiety that is well beyond run-of-the-mill level - if this project paralyses you as you've described, get out now before your health starts to suffer. Best of luck.

Pips,go apprentic with Rusty to get a feel for these type projects. OMG,a country church and a jail house,,,,,,,,underway at the same time? That's a load.

First, make sure that the roof is in good shape. Cosmetically, not the issue, just be sure there are no leaks. Make sure gutters & downspouts direct water away from the building.

I agree with ingeorgia...make a couple rooms your havens for now. Preferably your bedroom & a sitting room.

You'll be amazed at the level of "mess" you can actually live with while you're fixing it up. Couple things I cannot stress enough...

1...Live in your place for at least a year before making any changes that are irreversible. (removing walls, painting original woodwork, removing original windows)

2...Don't listen to the big box sales people. They will not direct you correctly on your journey. They're great for tools & supplies...but not anything that will be permanently connected to your home, like lighting or any fixtures for the kitchen & bath like sinks & toilets & such.

Just sit back & listen to what the house tells you...and trust me, it will!!

Oh....I forgot...more pics please!!!

Inside, to be more specific!! :0)

Great advice lazy_gardens! I'm saving to reference.

Pipsqueaky, what a charming home! I can see why you bought it, and also see why you are overwhelmed. I'd make a nice big list and sort it all out in a notebook. Sometimes getting it down on paper and out of your head offers some relief.

Lazy_gardens is right, deal with water issues first. Keep in mind that you don't have to do everything at once. Even if you had a lot of money, these things take time, and with a small budget you will be working on the place for months or years. So just relax and pace yourself.

If the house is in Germany, keep in mind that most posters here are USA, so building practices and codes are different.

I definitely agree that TWO rooms need to be "prettified" even in you have to redo some of the cosmetics.

Going in, shutting the door and pretending it's ALL DONE is a wonderful thing for your sanity.

I think I would hire an architect to help figure out an overall plan for the house, unless you are happy with its current plan. Think about how you want the house to work for you? Are there walls you want to move? Does the kitchen need to be gutted?

Once you have a plan, tackle the important things first, keeping in mind the overall design plan that you will develop in the future. Electrical, plumbing, HVAC, roof and exterior are some important things to start with. Next, I would probably tackle kitchen. Make a plan and take your time as budget allows. You will really be comforted knowing that the guts are in place before you start making the house pretty. I did not want to pay for new HVAC system in my house, but I can tell you I am so thankful I did now.

I am going through this with a 4000 sq. ft. home I bought four years ago. I did the HVAC, electrical, windows, doors, drywall, interior painting, and kitchen first. I also did the flooring and a guest bath which was a mistake and will have to be redone. I made the master bath useable with things off craigslist, as I knew in the future I would want to do something with it, but I didnt know what. 2 yrs. into it, I put on a new roof. Three years into it, I re-stuccoed the exterior. Last year I did the landscaping. Now I am adding a new master bedroom/bath and moving a bathroom. Within a year, I hope to have all 4 guest baths done and new flooring throughout the house.

BTW your house is really beautiful. The fact that you have lived in the house should be a plus, since this may have helped you figure out how you the house to work for you. I made the mistake of jumping in before I had moved in. Now I will have to tear out a bathroom I redid.

Do you need to get rid of that beautiful gorgeous tree?

You want the house to be made safe and secure first, with functioning HVAC, electrical, plumbing and roof. Possibly hire an architect to help come up with a functional plan for the house Start there.

Are you in Germany?

Since it seems as though most of
your confusion is coming from the decision of where to start, I would suggest that
you reach out to a few architects. Have the architects come to your home and
write a proposal. This will help to professionally assess the current condition
of your home.

From this, you can then develop a “master
plan” for what the ultimate goal is as of updating the condition of your
home. Once you have a plan you can then begin to conquer one project at a time
to the pace of your budget.

Notebook all the way. One section for each room/roof/basement/exterior/landscaping. Then after you have it sorted you can more easily see what is an emergency, what needs to be done soon and what you can do one room at a time. The volume of projects you are looking at right now overwhelms ME and I'm not even involved! Small steps. The longest journey begins with the first step. We'll be here. Keep us posted.

not the OP but I wanted to thank all the contributors for their helpful comments. Going through the same process right now, and after doing everything wrong thus far-- it is good to feel like we are not alone here and to have some guidance. My place is 306 years old, but full of 1960s-1980s poor quality renovations that need to all come out.