I have deep emotional ties to this home.

Allowing a problem to persist is not the lesson you want to teach your sons and that’s far more important than the temporary discomfort of addressing the problem head-on.

@Leah DunnellsThis is my system for keeping track of expenses and making tax time less of a pain.1)  I keep a "Temporary" folder where I put receipts for supplies, repairs, and maintenance which I have already paid but still need to document for taxes2)  Along with the temporary folder I collect any bills coming in from the utility companies3)  Every 2 weeks sit down and pay utility bills through Chase Bill Pay4)  Once bills are paid I will document both the receipts in the temporary folder (step 1) and the bills I just paid (step 3) in my spreadsheet5)  Spreadsheet is in the form of a Schedule E with all the same sections to make taxes easy at the end of the year. 

Also, am I being emotional pulling the deal.

That’s a personal decision only you can make .for many owning their home is deeply personal and emotional matter ( myself included)  I know I surely wouldn’t sell my families home simply because I can’t get a tax incentive on it or other houses went up in value around me .

The 99 aging reactors left in the US (and an olympic-sized swimming pool of radioactive waste from each one of them sitting around in temporary storage with nowhere to go) may just be our country's biggest liability.  

Investing is about prudence, patience, and emotional detachment. 

Here are five “golden rules” to buying investment properties.Rule #1: Leave Emotions BehindWe all get attached to an idea, a vision, a plan.

Taking a different tack on this... sometimes it is not always about having the logical "by the numbers" discussion but rather is more about dealing with fear and emotions.

In regards to getting over your fear, learn the market, buy based off numbers and not emotion and go for it.