The mortgage you hold on your property is not the item that would hold up a purchase.  

By the end of 2016 my basis in the property is about 30K getting it ready for sale.I have not plugged in a value for the donated items, but suspect using one of these donation calculators in TurboTax or equivalent it would likely be around $5,000 to $7,500 - more than the purchase price.Should I write this off from my end of year basis or would the IRS say I could only write off a small % of the $2,500 as that reflects the market value of the home and contents - even though the county obviously had no idea what was inside...or maybe the IRS would say once I found the contents to valuable I would have to recognize a gain.  

The other item might have been that your home might be more desirable to own than to rent.  

I think that is a great idea, but I would not sweat not owning, heck, sometimes I wish I rented so that I could call my landlord to fix items and use the extra Fannie Mae spot for another home.

I also should have known to look at these items as I've worked in Real Estate for awhile.

Or the CPA might help prevent you from claiming a depreciable item as an expense, which could get you into fine territory.A CPA can knock these things out with one calculator tied behind their back.

If he didn't want to be charged for the items then he should have had them repaired PRIOR to the move out date and when keys were turned over.What exactly is he arguing about?

Is there a law that specifically prohibits the closing company not to disclose the buyer's itemized closing costs ?

In addition, some operating expenses are not NOI expenses, so you need "above the line" and "below the line" to allow for those items, such as advertising and commissions.

You are wise to keep an eye on every line item, just be open-minded in your approach to handle each item.