But these stories, and the volume of new buyer clients we're working with, are persuading me that the Mile High City might be okay for homebuyers and investors moving forward. 

It may be scary at first but a thousand miles start with the first step, you just have to start somewhere.

Came home one day and said they needed to drive 1500 miles for cancer surgery.   

10 miles 10,000 miles, if your an investor it does not really matter.  

In other words, going an inch wide and a mile deep is a way better use of time than the opposite.

Appreciation has been great and there are 6 flips within .25 miles so I’m excited to see how those go and if they bring up values again.

With that being said, I would recommend staying away from certain neighborhoods south/east of downtown though - due to your timeline, certain spots are heavily saturated and you may have trouble competing in that market in just a couple years when you're ready to sell.

How many miles are you going to put on it per year?

The house is in Clairemont, San Diego about 4 miles away from the beach.

Great school system, close proximity to Boston and the Seaport (10-12 Miles), orange line accessible, holds value very well, and more for your money compared to the other two towns mentioned.