Man, I am in a weird sort of the same situation, if only in existential bits and pieces. Without knowing the full background, have you considered having the farmland parceled and keeping the family home, and using at least some of the proceeds to have the required maintenance done? As far as the sibling goes, that’s another tough nut to crack. My mother is 80, and several years ago we all decided that the family home that was built when I was an infant was going to stay in the family. Subsequently, my youngest sister (approximately your sibling’s age) had a nervous breakdown during a messy divorce, lost her job, moved back into the home, invested a good chunk of money to remodel the downstairs as her private apartment, and now the middle sister is giving me guff about feeling like I somehow have some sort of birthright to a home she wasn’t even a zygote when it was constructed, and it would be sold to pay the taxes and other expenses. And this all evolved without my knowledge or consultation. Needless to say, she can go piss up a long rope in a stiff wind. So, I don’t have any advice other than to follow your instincts on this one. Don’t overthink it. When your gut tells you ‘yes’ or ‘no’, follow it. Given my mother’s health, I may be doing that in the very near future. You’re the executor - don’t get manipulated.
I did think of the parceling, but the way it is three siblings have homes/large lots on one side of the property so any parcels would be sort of useless as there is no frontage. There is frontage that could be sold.
I feel for you. That is tough. As one of my relatives said when talking about distributing family property... “There is ONE in every family.” In other words, someone makes trouble and seems to want everything. (Not my situation)