In those years, I had tenants doing an adequate job, to ones where they don't get to mow till it's over 6 to 8 inches long and neighbors complain and threaten to call the town.I found tenants who take their mowing seriously are blue collar family types.

In my experience, if you are seen as bringing investment and job creation into the country vs coming to the U.S.A. to work (the theoretical "taking jobs away from Americans"), there is never an issue.Another bit of advise is to answer the border agents questions as succinctly as possible and do not volunteer additional information.  

Of course this doesn’t affect income tax owed on my oregon rental income or job income generated in Oregon

I suggest building up some cash either by wholesaling or your job HML will only charge fees that could be put in your pocket. get the experience in first before you start flipping with your own credit you will not be upset.

So when the day came that I walked out of my b*llshit soul-sucking corporate cubicle job, I had a decision to make; "Retire" for 5  years or invest in myself and my future with the money I had. 

Maybe you can list some of the types of jobs you've done?

I don't want to "Put lipstick on a pig" but I want to do a nice job. 

Are you paying for the job or paying hourly?  

Your fiancée would benefit from looking at getting a w2 job because off the books income is not going to count.

I relocated back to my hometown of Memphis after retiring from my job of 27 years.