I am drawn to the idea of minimizing my housing expenses through house hacking and understand multifamily homes such as duplexes and triplexes are difficult to come by in Portland proper.

I've absolutely seen that some lenders can do that, and FHA guidelines allow it too which makes it even better, but pulling the trigger on the property would still be very difficult for me right now due to credit issues—if I had even 2 more months I'd be singing a different song, but alas. 

“Since the Legislature passed House Bill 4213, thousands of people have been displaced by massive and devastating wildfires, and the global pandemic continues to make it difficult for many Oregonians, including Oregon’s veterans and many families with children, to pay rent, through no fault of their own.” 

In contrast inner city properties are a different story, a market with a different dynamic: poverty and crime are high, it is sometimes difficult to sell a property, because nobody who can qualify for a loan wants it or the loan amount is so small that no bank wants it.

my fear is that if I just purchase under my name, it would be difficult to qualify since it was not purchased under an LLC?

The recent surge in sales in my area has made buying anything at a reasonable price difficult. 

What do you think makes OOS investing more difficult for people starting out than investing in your own backyard?

Turns out the appraiser hasn't pulled comps yet, and says "this is a difficult area for comps, I need some more time..."

Landlord insurance policies on mobile homes on rented lots can be more difficult to obtain.

For example, it may be difficult to give away money if we only have enough money to survive paycheck-to-paycheck ourselves.