What do you do when their isn't enough money for house repairs?

our house is 35 years old and I the people that lived here the whole time didn't do much to it. No updating at all (not necessary for us to live here) and bare minimum on upkeeping the essentials. So the roof has a leak over the garage and really needs to be replaced all over. It is the second layer and is pretty old. We had someone look at it and we were told it wouldn't last much longer and of course it has the leak.

The fireplace is extremely drafty, there is literally a cold breeze blowing through the den all winter. We keep a big moving blanket over it, which helps, but that room is so cold. We looked at getting a new damper that would seal it up perfectly and installed it will be $500. Dh wants to do it himself, but we don't have a big enough ladder to do it, so we would have to buy it, which brings the total back up to $500. But I would rather have a ladder than not, so it would still be better to do it ourselves rather than pay someone.

Then the driveway is a complete wreck. The kids can't really play on it it is so torn up and riding scooters is impossible and bikes is a little dangerous. The kids can (and do) literally pull up strips of the ashpalt. We are in the middle of getting estimates to replace it and of course the whole thing needs to be dug out and redone. The lady called and the city has a rule that if you do that you have to replace the drain pipe that runs under the driveway, which of course really adds to the expense.

So we have all these big expenses looming and virtually no money to cover them. What would you do? Pull some from the EF? We don't have enough to cover the roof and I don't know about the driveway. I do think that the driveway is the last priority here. I am just so frustrated with all the places that need our money and not enough money to go around. I am also sad because I had hoped to sign up my dd for gymnastics this year, $44 a month, not too much, but when we have so many other things that need our money I can't justify putting her in. But then I think well then we will never have the money for it all, so i might as well just sign her up. I guess I am just frustrated and a little depressed at the money situation right now. How do y'all handle times like this? Thanks!