You would claim the casualty loss for the roof and the vehicle on your 2020 tax return as one casualty event.
You figure the loss for each item separately and then use the combined loss number on your return.
To figure the loss for the personal residence you have some safe-harbor options that include either using the insurance estimate or the contractor estimates.
The safe harbor methods for personal-use residential real property available through Revenue Procedure 2018-08 are the following.
• Estimated repair cost method.
• De minimis method.
• Insurance method.
• Federally declared disaster method—contractor safe harbor.
• Federally declared disaster method—disaster loan appraisal.
See page 7 of this IRS Publication for an explanation of each.
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