There's a lot of moving parts here but it sounds to me that you owe them at most the original $150k + a conservative 8-10% interest per year (well above market rate).

Great occupancy rate, congrats!

And I could have lower income in that window after I semi-retire, before my mortgages are paid off to take advantage of a lower marginal tax rate

And most are variable rates.

With no experience you may have a bigger interest rate but if you have good margins on the hose, you should be OK.

I really do try my best to be an awesome landlord, but it’s starting to not feel worth the time and energy.The house is at a 2% fixed rate so it’s hard to consider selling (at least right now), and getting the tenants out of the house would cost at least $5k per the Portland laws.

Is there partial fixes (ie. new roof, wind resistive windows and doors, etc.) that will accomplish what you want on reducing the rates.

Here are the #s:Asking $129,0002 bed 1 bath 718sqftEverything has been updated15% Down - 9.5% Interest rate - 30 yrs amortization, no ballon Rents around $1000 - 5% Vacancy - $700 Taxes yr - $741 Insurance yr - 10% Property Management - 1.5% of rent for Maintenance and 5% of rent for capital expenditures. 

My current APR is 7.15% I'm pushing towards the HELOC because lower cost on closing costs and refi interest rates are the same as my current loan right now. 

The rate quoted was 8.875% so I really want to stay close to that as well.