Talk to local property managers, investment agents, and others involved in in the real estate in the area.

This could involve adding new information (e.g., embedding a link to a ski shuttle schedule) or setting expectations (e.g., noting that there’s no A/C, which is an rare amenity in our climate anyway).

With the cash flow number and the potential equity gain every year you can calculate your estimated return on equity - my hunch is that with $500k in equity it will not be great return.Another thing to keep in mind is that if you have lived in the current house for at least 2 of the last 5 years and it has appreciated a lot while you have owned it then you can sell with little to no capital gains (there is a limit that you may be pushing with that much equity).For those reasons I would probably consider options that involve selling.

Typically if there is a co-borrower involved lenders are going to use the lowest credit score to qualify. 

Marketing homes during this period involves creative strategies, such as seasonal staging and targeted online promotions, to attract buyers even amid holiday distractions.

Don’t be involved with those properties in ANY other way (management, lending, repairs, etc.) 

I live in the US and some of the questions I have involve lending options to help me out with the construction loan and approaches to managing the property as a short-term vacation rental.

Here's the bottom line- I know that there are opportunities that do not involve fix and flip that you may be able to bring to an investor who will then decide to invest with you based on the numbers.  

If you want to be able to fly out, Calgary or Edmonton are your best bet. 

This is a perfect time to get your qualified intermediary involved if you don't already have one.