Quote from @Joshua Alcantara: Quote from @Peter Walther: I've found many properties with title issues wind up with unpaid property taxes so checking on delinquent taxes, tax deed sales and lands available for taxes might help you identify some.Thanks, Peter, for the info!

What you owe doesn’t affect how much tax you owe. 

Even large and small businesses with intangible residual services like TV, internet, security, pest control or the local contractor with remodels in process could fall behind on payments revenue contract. 

My son currently lives in the townhouse b/c he is going to school and works in the area.Since he is young and starting out in life, I would like for him to only cover the basic costs (taxes, HOA, utilities) just enough for me to break even (I believe that will put him slightly little lower than market rent rates). 

But ya have to make some educated prognostications in life.Add this to the information your processing - What your talking about doing is eliminating around $4000 or interest expense (which is deductible anyway so really could be a real impact of eliminating $2800 or so) of debt in exchange for paying over $10K in capital gains tax (don't forget possible state gains tax as well).  

Taxes are private, 1099 are private.  

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You’d also make all future capital gains at least partially taxable instead of tax exempt by converting your primary to a rental.

I should have been more clear...I actually have a BLOC with multiple properties securing the interest.

This would allow you to defer the capital gains tax, and instead of taking a large tax hit, you would be able to use the tax to invest in a nicer property/properties.