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

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

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.

There are not a ton of comps on Zillow or other websites that I have checked and it was last sold a while ago so even these resources are unable to give me a quote.  

In short, I can afford the additional $1100/mo cost of a second house, even until I rent it out.I have around $35K in HYSA and emergency funds that I could use for a down payment, but that's less than 20% which would be required for a conventional loan, assuming full purchase price.

We don't even call them "attorneys", we call them "lawyers".

-Even if reclassified as real estate, it would still be seen as manufactured or mobile home, and would not appreciate in value. 

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.  

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