The issues raised by your question involve a number of different legal concerns.
You currently own your home outright and free of a mortgage. That means as long as you pay your taxes, the home is free of the claims of your creditors and is yours to do with as you please during your lifetime and at your death (unless your children a minors - younger than 18 - at the time of your death).
If you transfer title to your boyfriend, you will own the property with him as either tenants in common, or a joint tenants with right of survivorship, depending on how the deed is prepared. As tenants in common, you will own your half, and he will own his half. At the death of the first to die, the deceased spouse can give his or her share to anyone they want. The survivor retains the remaining one half share of the property. If the ownership is taken as joint tenants with right of survivorship, then you each will own your 1/2 interest, but at the death of the first to die, the property will automatically and immediately be transferred to the survivor by operation of law, and there will be no interest that can be transferred by the deceased spouse to anyone.
Under either scenario, the full amount of the mortgage will continue to be owed by the survivor of the property regardless of whether the property is now owned outright by the survivor, or only one half of the ownership of the property is with the survivor.
If the mortgage is not paid timely, the lender will have the legal right to foreclose on the complete property and force the sale of the entire property to pay off the mortgage. If the foreclosure results in the sale of the property for more than the amount of the mortgage, then the excess proceeds will be paid to both you and your boyfriend, and it will be up to the two of you to decide how to split those excess proceeds.
A revocable trust may be useful to accomplish your purposes, or at least some of them. However, a revocable living trust will not avoid your boyfriends medical or other financial obligations, which could result in a lien against the property if your boyfriend moved out of the house and did not occupy it as his home.
Your other properties should be dealt with separately from your home. The biggest issue for you to consider with those properties is the potential liability that can arise out of the ownership of rental property. If there is an accident or injury on the premises of any of those homes, it is possible that you, as the owner of the property could be held liable for the damages incurred by someone injured on the property. You may want to consider a limited liability company or a Florida land trust to protect yourself from such liability, and you certainly want to obtain a comprehensive umbrella liability insurance policy as a first line of protection for those properties.
It is important for your financial well being that you seek counsel with regard to these matters.
Good Luck!
Answered on Dec 16th, 2012 at 2:34 PM