Also, i have two rentals in this market already... both of which have risen in value by about 30% over the past two years. 

Then you can do you your rehab and then refi in 6-12 months after the value has risen from the rehab.

Her rent had risen from $875 to just under $1,000 a month over the course of eight years.

However , the market has not crashed and median prices have actually risen.

So you can certainly increase the rent to a number that is below asking rents elsewhere AND not lose the tenant, especially where your tenant has been there a number of years; you just explain that as your expenses have risen over time you absorbed those increases, but now realize that over time those increases will have to be passed along to the tenant. 

State you are leaving rent the same (even though rents in the valley have risen 4% yoy), but no longer paying for this and that utility.  

My 1099 was from a business that I had worked for steadily for 8 years, and after the financial colonoscopy required for me to get a loan (on my income alone), I'm not so sure that buying a townhouse in a cheaper area was so much better financially than renting.

I only raised the rent $10, but explained to the tenant that the condo fee had risen by much more.One time I bought a rental with an existing tenant, that the owner had never raised the rent in many years.

If they're paying 1.5k from the 2% rent increases while market has risen to 3.5k there's no way you're getting them out.

Though the building’s expenses and property taxes have risen significantly, and though average rents in Portland have increased 14% year over year, your rent will only increase by 5%.