Also, while having all my eggs in one basket would limit some costs, it would also mean a larger loss if the property is vacant.

) $0.00 $0 General Vacancy Loss 10.0% $9,240 Expenses Monthly Annual Fixed Electricity $0.00 $0 Water $66.67 $800 Sewer $0.00 $0 Garbage $15.50 $186 HOA $0.00 $0 Insurance $415.00 $4,980 Taxes $448.83 $5,386 Other $20.78 $249 Variable Repairs and Maintenance 3.0% $2,772 Property Management Fees 20.0% $18,480 Other Capital Expenditures (Reserves % Gross Income) 3.0% $2,772 Market Assumptions Market Rent Growth (per annum) 2.0% Expense Inflation 2.0%

He checks the main items--roof, foundation, hvac, plumbing, electrical, structural...but doesn't do a deep dive into the cosmetic issues or small items.

Also, most item lenders over estimate the closing costs on the estimate by a little.  

My thought behind doing this would be twofold:1) I can deduct my home improvement expenses (cleaning, painting, remodeling).2) I can deduct the business loss from my personal incomeCan I do this?

Unless you plan to liquidate your portfolio at a loss.

Local company I can recommend is Leverity Insurance in Beachwood, Ohio  - you can ask for Joe Corradetti.If I am not mistaken: Actual Cash Value = coverage less the depreciation Full Replacement Coverage  = no depreciation loss and possibly will accommodate code upgrades (you should check the rider on it, to make sure if you do or do not have code upgrade)Always consider the worst case scenario, you may have to decide based on value depending on your projected financials .... so ask questions when you make your decision.Welcome to CLE! 

Notice, discounts are the items listed on line(1) above, so the factors are:need high GSI,low expensesand a historic low vacancies (ie you can beat the Vacancy rate)However, learn the Class {A,B,C} rating system and then be sure to buy A or B properties in growing communities and neighborhoods.

You ask about how to help prevent a loss in a crash.

I will follow the law and they must correct the items on the list if they plan on staying until the end of the lease.