When I set up a new property, I go out and spend a week or two and get it fixed up.

I am not sure how you could lose much money, when you are only spending $8000 on down payment.

I usually spend way too much time strategizing in my head trying to figure out the optimal way to get compliance without ruining the relationship. 

A lot of times there’s a decent amount of crime in your own area that you’re totally unaware of.”And it bears repeating, “The best thing you can do to experience a neighborhood is to spend time in it.

By leaving your equity in place, you're spending $250k up front to get $14,400/year...and, you don't make a profit until you recover all your costs. 

Are you planning to spend 18 hrs a day caring for your properties and tenants or are you going to have a property manager?

Therefore regardless this wholesaler would already have spend money, time finding seller, and market to still not find a buyer.

I was thinking about selling Commercial RE, however; I can't afford to do it because the investment business is more lucrative and I don't want to spend the time to BUILD an agent business. 

You may want to take step back and figure out what types of tenants you want to attract and how much time you want to spend managing your rental.

I wouldn't be living there full time but would love to spend chunks of time in Portland to see the family once in a while and make some money in the process.