I'm selling a 3 unit in Phoenix right now that fits the 1% rule, hard to find in Arizona no doubt but we come across some.

I sell insurance and prepare income tax returns but I am not an attorney and don't play one on television or radio.The Illinois Legislature has a law either pending or just passed that will GUT LLC protection.

Beyond carefully vetting the tenants, how can an investor protect themselves from squatters if we want to sell years down the road?

Adding and making better could sell or rent faster, but it won't get you more than what the market ARV and rent is set at from other similar comps in the area....and your Interior Design background will help, if you you it mostly as an understanding of cost. 

You wouldn't want to pop a 2% balloon unless you sold the property, but make sure you write it as assumable so you can sell it.  

I've heard too many stories of investors purchasing homes for STR use, only to find that they lose their permit or the ability to transfer it when they sell.

Several factors at play: the sales market has been slow so many would-be sellers are converting houses they can’t sell to rentals, lots of new construction units have been completed recently, and in-migration has slowed down a bit.

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.

Can we DSCR out of this to get our money back out or will I need to sell it to get our $136k total investment out?

 If you start selling houses in Virginia now 2.5 years from now your business would be humming along.