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You would have to file a claim for both vehicle and pay the deductibles for each vehicle. You cannot use liability insurance on your own vehicle because you cannot be liable against yourself. This prevents people from purposefully hitting their own vehicles.
From the Florida DMV website: "Existing law only prohibits the retitiling of an unrebuilable vehicle. It does not prevent such vehicle from being rebuilt or sold in a rebuilt condition in Florida, thus making vehicles available in what would otherwise be an unsafe condition for persons outside this state. To prohibit the rebuilding or selling of an unrebuildable vehicle that has been rebuilt in the state would clearly send a message to those who are redoing these unsafe vehicles that the state will not tolerate such conduct." A Certificate of Destruction (or C of D) is only issued when the car is unrebuildable (as deemed by the insurance company). These are cars that required more than 80% of the vehicle's cost to repair. If this were a salvaged title however, it may be possible to retitle it. So, in short, no you cannot.
Mobile device
Yes. You can add and have an obligation to add anyone who drives your vehicles. This does not mean that you can add their vehicles onto your policy. You cannot insure a vehicle that you do not own.
Such an endorsement does not exist - there is only an air brake restriction. Basically, if you're operating any vehicle requiring a CDL, you cannot operate that vehicle with that restriction if it is equipped with air brakes. For vehicles under 26,000 lbs. GVWR, this would include any vehicle carrying hazmat, or any bus designed to transport more than 15 persons (including the driver).
not if you chain it up with some heavy duty chains... But, seriously, folks... A landlord cannot "tow" any vehicle unless there are clearly posted signs that restrict parking for "tenants only" and they have confirmed that the vehicle does not belong to any tenant (e.g., by looking at the list of tenant registrations). If there are no signs, then it is presumed to be open for parking by guests and visitors and it would be completely illegal to tow any of those vehicles without first notifying the vehicle's owner.
It doesn't matter if he's unlicensed or not, unlicensed persons can own motor vehicles. The question is, can a minor "own" property in your state? In most states minors cannot legally hold property in their own name, if they appear on the title to anything it must be as a co-owner with an adult.