How should one bequeath a large asset (e.g. real estate) in a way that will cause the least disagreements among multiple heirs
Say that I have a large asset, like a real estate or a valuable possession, that I want to handle in my will. I have three children and would like to bequeath it to them (I don't think it would be fair to give it to just one or two children). But as shown in Bequeathed condo left to three children. How to sell if one party disagrees?, giving them equal ownership of the asset can put them in a very difficult situation if they disagree on what to do with it (we'll assume the the asset is not something like farm land that can meaningfully be split into multiple pieces).
What is the best way to handle such an asset in a will so that will cause as few difficulties as possible as they decide what to do with it? Ideally, I'd like to see a solution that doesn't involve stating in the will that it must be sold and then splitting the profits, given that there is often strong sentimental attachment to such assets and I'd hate to make them lose something they prefer to keep.
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The first step is to talk to your heirs and fund out if they even want the large asset. If they don't want the asset, then it would be far better to leave instructions in your will for the asset to be sold and then the proceeds distributed.
If only one heir wants the asset, then adjust their inheritance to offset leaving them the entire property. If multiple heirs want the asset, then work with them to figure out the arrangement that works best.
The key is that your estate planning should not be a secret from your heirs. Include them in the planning so that you are not doing something for their benefit that they don't actually want. Also involving heirs up front will help to avoid bad feelings when they get surprised by your will in your death.
So you've put the two obvious solutions out of reach. You can't just leave it to them and let them sort it out. Also, you can't just have the executor sell it and split the money.
Let them choose
You could let the heirs choose whether to keep it or sell it. If they choose to sell it, the estate can handle that for them and divide the money. This would also allow for two to vote to sell and overrule the single keep vote.
Mortgage
A two to one vote is still unfair to the one. So how to allow one person to sell or keep? Assuming sufficient income those who vote keep could take out a mortgage and buy out those who vote sell. If there are additional assets or monies in the estate, those can help reduce the mortgage required too.
This allows for any possible division among the heirs. If all three want to keep, that's easy. All three want to sell, also easy. Two want to keep and one sell? Not so difficult, particularly if the estate has other value than just this asset. One wanting to keep and two to sell is more difficult but may still be possible (depends on the one's income and the asset's value and perhaps profitability). As a backup option, if they can't all agree, you can default back to the sell and divide option. That's probably the fairest way to handle disagreement.
Valuing the asset can be difficult. One method would be to put it on the market for six months at the highest price. If it fails to sell at that price, use the lower valuation. This handles the situation where the one sell vote wants to be bought out at an unreasonably high amount. Another option would be to specify a valuation in the will or to specify an appraiser.
The important part is to explicitly allow this decision to be made before transferring title and to set up the parameters of the decision in the will. And as the other answer suggests, involving the heirs in this up front can allow you to address issues while alive that might be contentious without a referee.
Think like a nonprofit
Treat it like it's being run by an enduring trust, and the gift like a project managed by that trust.
What is the mission of the project?
Is that mission realistic?
Is the project realistically manageable? (is management achievable by any of several family members, or could it self-fund professional management)?
Is that mission self-sustainable?
If not, is it practicable to leave behind an endowment or user-fees to fund it?
Are these plans likely to survive the number of years until you die?
Have a written plan for everything
Stuff happens. The linked situation with Jane is utterly foreseeable. What you need is a senior litigator who does a ton of litigation in this area to pretty much write down everything that ever happens, and figure out a plan that resolves every single one of those things, without contradicting itself (or at least resolving a clear unambiguous precedence of how conflicts are resolved).
Normally I'm reluctant to say "hire a professional" but in this case you want a guy with lots of experience litigating exactly these kinds of issues; who knows what issues people fight over... what the state requires, forbids, or allows to be overridden... and the extant case law.
You want to make resolution as easy as possible for the intervening judge, not lay him any sticky questions, and so expensive litigation is fruitless and inadvisable.
Instead of being an estate, it can be a trust
By default, assets go into an estate, which is a type of legal "person" whose mission purpose is to resolve the affairs of the deceased, liquidate assets, and cease to exist when this is complete. Instead you can set up a trust, which is designed to operate indefinitely.
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