Now he has sold the company and is more of a flat rate charge based loosely on how long it takes him to prepare the return.

A title company?

The challenge was separating business from personal relationship.

Look into a DSCR, Debt Service Coverage Ratio, loan where the rental income can be used to qualify the cash out refinance instead of your personal income.To Your Success! 

You now don't seem like the type of person most of us would accept a recommendation from.

Someone to stock supplies, an appliance repair person, heating/air conditioning repair, plumber, lawn care person, carpenter, salesman, and occasionally an electrician. 

Let's break it down with precision:The "Pain" (At First Glance):Your $2.8M sale splits out as:Building (§1250): $2.3MPersonal Property (§1245): $500KOriginal Basis Allocation:Building: $1.6M (depreciated over 27.5 years)Personal Property: $400K (fully depreciated)Building Depreciation:Annual: $1.6M ÷ 27.5 = $58,182Total over 10 years: $581,820Gain Breakdown:Building (§1250):Sale Price: $2,300,000Original Basis: $1,600,000Less Depreciation: ($581,820)Adjusted Basis: $1,018,180Total Gain: $1,281,820Unrecaptured §1250: $581,820 (25% max rate)Capital Gain: $700,000 (20% max rate)Personal Property (§1245):Sale Price: $500,000Adjusted Basis: $0Ordinary Income: $500,000The Strategic Play:Remember those suspended passive losses you couldn't use?

It is great to see what your company is doing in the Milwaukee market!

With insurance companies canceling policies and raising rates has anyone uncovered a way to self insure rental properties?  

I would be happy to share with you Property Management companies and assist you with any advise if you send me a DM.