If you are low-balling the price to save on taxes, you run the risk that someone swoops up your property for cheap.
If you are low-balling the price to save on taxes, you run the risk that someone swoops up your property for cheap.
It's not fine for grandma. She doesn't have a team of analysts, she just wants her house. The main criticism of capitalism is that it's bad for the little people. Replacing it with something else that's also bad for the little people isn't really any better.
You could try to find compromises like locking the family home until death or voluntary sale... then you have extra complications like making it legal for someone to start a small business at their family home without also creating a grey market for people to rent their family homes for other people to start businesses in (or just to live in) and getting the system we already have.
You can't submit bids in this system without the intention of buying, if you have the highest bid you're forced to buy.
If you can demonstrate that the purchase offer is made because of personal animus, or the buyer has no reasonable and specific plans for the property (i.e. the billionaire buying out a small town without a workable business plan), then the courts would overturn it.
Ultimately, billionaires have lots of ways to mess with someone they don't like. If we don't like that, we should circumscribe what billionaires can do with their power.