If you are going conventional, they will need 2 years of tax returns, no way around it.We will use your "net income" after all deductions for 2022+2023 and divide over 24 months.

If you hire a contractor , you deduct what the contractor charges .

Insurance would cover it, I would pay the deductible, and no assets would be lost.If you are in an area like San Diego where people are more likely to sue, a judge is more likely to find you guilty, and the payout is expected to be higher, you may consider an umbrella insurance policy.

Travel and meals (50%) are deductible.

Insurance would cover it, I would pay the deductible, and no assets would be lost.If you are in an area like San Diego where people are more likely to sue, a judge is more likely to find you guilty, and the payout is expected to be higher, you may consider an umbrella insurance policy.

You could pull out cash tax-free and still benefit from depreciation and other deductions on the rental side, which could reduce your tax liability.Quick Tax Comparison:Selling:Capital Gain: $160,000Tax Due: ~$32,000 (at 20%)Net After Tax: ~$128,000Refinancing:Loan Amount: ~$263,500 (at 62% LTV)Tax Impact: None on the cash-outRental Deductions: Continue benefiting from depreciation and mortgage interest deductions.Refinancing offers liquidity without the immediate tax hit and lets you maintain rental income, making it potentially more advantageous.All of these are rough numbers of course, but just some different ways to think about it!

Which ever home you choose as the main home it will be a tax deduction so it should work out in the long run.Another thing to consider is having two primary homes does not offer a great Schedule E option where you can have the bigger tax shelter. 

But I'm wondering if there is a way my parents or I can claim mileage deductions on taxes for my travel related to taking care of their properties.

This will be your leverage if you decide to get under contract because you can deduct all the line items that need to be fixed, potentially being able to grab it for a deal.

*Could we deduct the expenses of any modifications made to make the home more accessible (ie adding a ramp to the front door)?