Those are tough to make a call on sometimes. You should do some detailed assessment of all the work needed and see if you can put a labor number on it, as well as a quantity take off, and compare against a new one. That may help decide whats feasible, but as many of us know with old equipment and such, feasibility sometimes goes out the window LOL !
New would be nice, potentially safer, not sure about insurance, also built to suit your needs, less potential labor, (if building your own), not as complicated as a repair to the old one.
It looks as if the roof is fairly straight, but if theres a lot of work to get it straight, do consider the danger in such work, as well as the experience needed to know how to address and employ the best methods to safely repair it.
One can appreciate old barns and buildings and I'm all for saving them for a useful purpose if can be done, even if its borderline given the condition, but there is a point where one needs to realize its not feasible, hopefully yours is, your dad would probably really enjoy seeing it repaired, but maybe he'd also appreciate something new just the same, suited for hay as you have been working towards doing hay if I follow your posts correctly.
We'd need some better photos to comment on any details or so I would think.
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