Additionally, how many calls does it typically take you to successfully close a deal using this approach?

I'm a big fan of value-add opportunities, whether it's buying something currently undervalued & fixing it up to my standards, or buying something that has additional income opportunities that have yet to be incorporated. 

Additionally, the beach is still within reach...just a short 1 hour flight or 6 hour drive.  

You can claim to be the best guy in the world at finding and analyzing deals, but when the market turns against you, and you just went all-in, even on the best relative opportunities that market had available at the time, there is nothing you can do to prevent losses, especially if your debt has a maturity date that will force your hand.Timing the market is an interesting concept. 

The only reason he did it was because it led to additional work.

After that's under control, focus on increasing income through additional work at your current job, taking on a side hustle, or finding ways to increase income on your existing rental.At the same time, educate yourself.

Consider lease optioning the “now keeper” and walking the created debt forward if you lease option buyer can cash you out. 

How much weight do you give to the cash flow benefit of cheap debt when the property is priced above market?

It was held by the previous owner for a very long time, so I wouldn't be surprised if some basic facts about the house are incorrect.I was making an offer on a house a couple years ago and discovered that the owner was paying taxes on an additional house that was on the neighbors lot and didn't know it!

You're also able to work with the utility company to install an additional meter.