Is that why you’re leaning toward renting, even with a $1K/month loss?

This can be especially appealing for those who enjoy traveling or seeking occasional getaways.

At some point, the juice isn't worth the squeeze for us and we just want to enjoy life. 

I have no social sphere or contacts family or friends in Oregon (I don’t know anyone besides my fiancée).Goals: continue to have flexible schedule while enjoying what I do (selling real estate) and making good money.

Even way out in the middle of the moutains where I am.

You'll need to really look at yourself and understand what you do well and enjoy, at the end of the day if you enjoy what you do you'll have more drive be successful everyday. 

I lived well below my means, worked a full time job for years while doing this on the side, persisted when others did not... and now I am enjoying the fruits of my labor.  

It may even be higher than 5% depending on the area. 

Expense ratio, as others have stated, often ends up evening out these fluctuations in each expense and can often times be a more accurate predictor over many data points.

Even if straight off a cliff.