If your goal is financial freedom, which is a long-term goal, not so much.Financial freedom is a long-term proposition, not a one-time event.

In the long run, I want to have properties that are producing strong cash flow (eventually would love to own small apartment buildings and syndicate larger deals), but it seems that focusing on cash flow and reinvesting those cash flows will be a slower process than focusing on properties prime for appreciation or with opportunities for forced appreciation.

Cost segregation is best for long-term holds and should be carefully planned with a CPA to align with your broader tax strategy.This post does not create a CPA-Client relationship.

If you had $50K in a Self direct IRA how would you leverage that to yield short and long term dividends? 

However, I probably would not upgrade it but I would rent it out LONG TERM at least until you know your long term status in Portland.  

If it has any basis at all (such as you left the apartment during your lease term for what you felt was a justifiable reason and stopped paying rent, but the landlord disagreed) then you may be better off paying a rather small settlement.  

Price fair, don't get greedy, play the long game.

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However, I'm drawn to the long-term benefits of multifamily properties.

@Robin Simon I completed a refinance with my credit union at terms of 3/30/75 @6.85% I will have the renwal in 2026 and hoping rates come down a little by then.