Bob, it is far easier for me to say what might be problematic strategies rather than give thoughts on what actually might work.
First off, my DH and I hold our assets jointly. I decided our risks of being sued individually do not outweigh the advantages and simplicity of joint ownership. We have good liability insurance with a two million dollar umbrella. I have good malpractice insurance.
When we had rental property, we held each property in a separate LLC. This provided at least some liability protection.
In contrast, I have a married couple as clients who both are involved in separate business ventures with separate risks. They keep their assets separate so if one loses everything, the other won't as well. They are Minnesota residents which is not a community property state. Therefore, neither is lliable for the business debts incurred by the other. If you consider holding assets separately, there are complications based on whether a state is a community property state and whether the state allows tenancies in entireties. Oddly, in some community property states a person can be liable for the debts of the other spouse unless certain formalities met, no matter how title is held.
Retire@40 mentioned family limited partnerships. I pointed out that they are not neccessarily bullet proof. However, it does provide a layer of protection. I believe there really needs to be a legitimate business purpose for the FLP. It is not a proper vehicle for your house and vacation home. Nevertheless a number people use FLP and LLCs to move assets such as vacation homes slowly to the next generation by giving gifts of interests in the FLP/LLC each year. This strategy is vulnerable to attack because of the lack of a business purpose. However, FLPs and LLCs can be decent vehicles for moving business assets to the next generation. However, there are often better ways to transfer businesses to the next generation, such as though basic corporations with voting and nonvoting stock.
It is helpful to know your own state's exemptions. For example, I believe that there currently is an unlimited homestead exemption in Kansas, Florida, Iowa, South Dakota and Texas. In those states, certainly don't transfer your home to a trust or any other vehicle as you might run the risk of losing the exemption. I would pay off a mortage on that home before ever paying off debt on a cabin or other non-exempt property.
Other states don't have a specific homestead exemption or a stingy one, so you should think about ways to try to protect the home in those states. States that come to mind which are problematic include DC, Delaware, New Jersey, Maryland, Pennsyvannia, Rhode Island, and Ohio.
One option to look at is a trust. If a trust is revocable, it isn't going to do you any good. However, if you set up an irrevocable trust you lose an element of control.
One problem with giving the next generation an interest in your assets before you are gone is that the next generation may have their own creditors. I was trustee in a number of bankruptcy cases where mom and dad put their home in a life estate with their children having "equitable" title to the land. I was always able to recover something for that child's interest and in fact, there are tables to value that interest based on the parents' life expectancy. Also, divorces by the children can cause a number of problems due to claims by exspouses.
Other advice gained from 20 years of bankruptcy experience:
Don't go bare on insurance unless you have nothing to lose
Don't guaranty the debts of your children
Don't be enticed by the pleasures of gambling
Don't borrow money from your retirement plan
Pay your taxes no matter what
Pay your child support no matter what
Pay your credit cards in full each month
Pay off your house
Live below your means
If you are a risk taker, try to position yourself so you don't take your family down with you if things don't work out