However, sometimes having a lot of resources can get overwhelming and I would like to stay laser focused in my pursuit.

Unless you are one of the very rare people able and wanting to fill up their days and nights with intensive, time consuming and exhausting numerous monetary pursuits I don’t see how your accomplishing your goal of simplifying and downsizing your life.

If you are actively managing something you need to place some value on your time and compare it with how you could use that time in other pursuits. 

@Pope Lake, as others mentioned, these are considered "Pursuit Costs," or the cost of doing business when purusing deals therefore they become a sunk cost.

The occupancy with two rentable units is greater than if it was just one (sounds obvious when you write it out)One thing to note from my experience on the same pursuit is lenders won't consider rental income from your primary residence as earned incomeI am big fan of seller financing into a house hack, stabilizing it, and moving out. 

I regularly comb through the MLS and run the numbers on properties in the pursuit of a deal that I can present to an investor (providing me the opportunity to be the buyer's agent now and possibly the seller's agent in the future) but as you know, that is the most competitive marketplace and deals are getting harder and harder to come by.

Good luck on your pursuit and let me know if I can help answer any other questions.  

I wonder if you added up all the income earned by "wholesaling" real estate, and divided by the total number of hours spent in this pursuit, how much BELOW minimum wage the amount would be?

If out door pursuits are important to you lots to do close in to PDX.. 

@Ken LatchersWhether the business of StR arbitrage turned out good or bad; whether the decision was incorrect from the beginning or just a victim of an unlikely occurrence, I applaud the initiative and effort of those who were willing to take a risk in pursuit of creating a successful business and a better life’s for the,selves and their families.Many on this forum advised against the arbitrage route, and I believed that they had many valid points and may have been correct for most people, who went in undercapitalized and without realistic expectations.