I use "The Best Self Journal" - (bestself.co) and it has drastically changed the way I enter each day and evaluate my production.As a last resort, if you must go back home, devise a plan for yourself to be out within a few weeks or months. 

The recommended entry budget is the starting point for your investment amount where you will begin to find a profitable short-term rental.Panhandle–Beach destination; somewhat seasonal; recommended entry budget: $500K South West–Beach destination/snowbirds; somewhat seasonal; $400KCentral East–Beach and events destination; seasonal; $280KCentral West–Beach destination; mostly seasonal; $400KSouth East–Beach and resort destination; year-round rentals; $500KCentral–Theme park destination(events/resort/family); year round market; $300KFlorida Keys–Beach, boating, fishing, family destination; mostly seasonal; $500K

People in Colorado don't want to have to deal with the snow but also we have lots of toys; expensive bikes, skis etc.

Websites would be my last resort.

You live in a master planned, sub divided neighborhood and 45 miles away there is a lake community you want to buy a house to get away with the family because you guys like to ski and fish.  

My Primary goal is to live in a home in an area relatively accessible to the mountains, ski resorts, and the city.

Originally posted by @Scott Mac:Run down (Slum) 4 plexes go for $600,000 WOW.Do you know how many SFH's you could get in Detroit for that--Just WOW.Kelowna is lower BC mainland on Lake Okanagan also basically the warmest area of all of Canada along with a huge retirement mecca,  tons of great golf wineries  fruit orchards  Big white ski mtn 35 mtns  the lake it self is about 50 miles long and great for boating and recreation deep blue water. then the mtns are loaded with fishing lakes its really quite the place and this is big for semi Rural BC LOTS of medical..

A lot of cities and towns (even mountain resort towns) are cracking down on STR and regulating them to the point of not being allowed. 

I am closing on a nice ski condo in Breckinridge Colorado.

This business is hands on, and I just don't see how you can do this remotely while backpacking or skiing all day like people will tell you.