You are selling an off-market property at a deep discount to someone else who wants to come in and make the repairs.

Lots of deep layers to this question.

If your tax person hasn't dug deep enough into this new issue to come to this conclusion they  may not be specialized in real estate. 

I don't know what your market rent is but I can guarantee after that deduction and all expenses the property will be deep into negative cash flow..

But I am sure there are deals but you have to dig deep.

If you dig deep though sometimes you can find a good deal on properties that others may have overlooked.

Full Whirlpool stainless suite, Bosch, LG, deep discount Mikes appliances in lime green?

This tells me that assets that don't have deep value adds available will be wiped out at some point in the cycle since rent increases won't outpace debt increases on the assets.I see people closing deals at $100  a door on adjustable debt in a rising rate market.

Is it normal for a lender to dig so deep in my finances?

Unless you have really deep pockets with cash to start like tens of thousands or MORE then you might consider working for an investment firm.