Ryan Dossey  this is the exact reason these homes go through this cycle. you have  a new investor buying in a very challenging area.. the success rate for more than 36 months is no more than 50/50 ... if you want to see what your urban core rental will look like in 3 to 5 years.. well your looking at it when you buy it and it needs major reno... in my mind this is the province for very experienced landlords that have hundreds of these..

I'd love to hear the challenges you face selecting tenants.

We, together, are learning, making money, and building a great network of workers to get us through the present and help us build the future.Bottom-line: I think you need “pleasant nightmares” to grow, expand, challenge yourself, and ultimately create what you envision.

Therein lies one of my challenges.  

When I put these together my biggest challenge is the lack of bookkeeping.

@Jonna Weber this will be challenging. =)

We wrote the seller a letter about the appraisal challenges (bank not lending above appraisal, and that other buyers would have the same hangups) and they accepted our offer at appraisal price of 170K.  

Then it just challenges people to find better deals! 

What are your biggest challenges in having Short Term or Vacation Rentals? 

The challenge is to always be replacing a new flip with one that gets sold.