Your success story is still being written.Love what you do: If you’re not doing what you love, you cannot really claim yourself a success.

Not claiming to know, just asking questions here. 

I'm not an insurance professional but I am a real estate investor/manager; which ever route you decide I would just highlight that you are getting insurance for a reason and it defeats the point to have 'coverage' that will not cover you when you most need it or go with a company that is not stable to support your claim should you ever have one - Me personally, I'd rather pay a bit more for absolute coverage that to pay cheaper premiums and one day turn for help from my company only to realize that they won't.... but the premium was cheap.

My goal is to flip regularly with a long term goal of holding multi-family units as rental income. 

@Adam FrancoFlips are recorded at your regular income tax rate, subject to self-employment tax.You figure out your final cost basis (purchase, rehab, insurance, property taxes, financing, permit fees, commissions, utilities, etc.) and the difference between the sales price and the final cost basis is the profit made that will be taxed as ordinary income.You should speak with a CPA to help organize things and try to minimize the tax impact.

If I'm using the standard mileage rate for 2017, can I also claim my business use percentage for my auto loan interest? 

and the relative lack of rentals, you'll have no trouble getting market rents or higher going to regular route.Best of luck!

The rest I would consider maintenance and upkeep regardless of how I claimed them tax-wise (i.e. faucet= maintenance expense, new roof= capital improvement).

Our plan is to take her security deposit to pay for the replacement of the carpeting and to write her an invoice for the remainder of the bill and take her to small claims court if she doesn’t pay the outstanding balance.

As @Steven Hamilton II points out - if you got insurance money, it was reimbursed - and therefore can't be claimed as a casualty loss deduction.If your casualty happened in a federally declared disaster area you can apply the casualty loss to the previous year's tax return (by filing an amended return) and it might get some money in your hands sooner. https://www.irs.gov/pub/irs-pdf/p547.pdfThe situation is continuing to unfold, so unless you were desperate, I'd wait.