That blows for owning a house 20 years.If you sold and bought the two other houses instead and they doubled in 20 years, you'd have two houses close to being paid (you'd still owe about 65k each) off that would be worth 800k total.   

Fastest growing company 3 years in a row now - blows away the school of hard knocks.

Outfit the space as turnkey for an appropriate business (smoothie shop, dry cleaning substation, etc.) and sell the “business” with a small down payment, receiving a monthly payment for the business payoff + rent/3.

These "hipsters" are young college grads who will live in areas that are (A) relatively inexpensive, (B) low or trending down in crime, (C) close to attractive civic amenities, and (D) are close enough to jobs. 

-Sauna-Hot Tub-Patio/courtyard (large cement tiles on crushed bluestone with lighting, natural gas line to bbq)-Secondary patio off primary suite-Losing sq feet in the primary bedroom to enlarge the bathroom-High grade cabinets-Appliances with cabinet fronts-High end appliances (Viking/Miele instead of GE Cafe)-Outdoor shower (teak box walls with a dry well beneath the footprint)-Wiring for Cat6 to every room-Wiring for surround speakers (or including the speakers that are built into the walls)-Sonos whole-home audio system-Hardwired cameras (with on-site storage) to the exterior of the house-Smart features: thermostats are a given, but how about light fixtures, switches, aromatherapy, fans ... anything else?

A better market would be dry arid regions like AZ, NV and parts of CA. 

When discretionary spending dries up, travel typically plumets.

Sometimes it will seem great, but then it gets it horribly wrong with confidence.While most exchanges are relatively vanilla, using an experienced QI and tax advisors in the process is well worth the avoidance of blowing up a 1031. 

Saw it go great, and I saw it blow up too.There's lots of moving parts to buying an asset, fixing it up, and selling it for profit. 

With the roof the other issue you have to consider is blow off.