I am thinking of starting with rentals, be it short term, midterm or longterm. 

Listing your property there ensures visibility.Build Relationships: When agents reach out, respond quickly, highlight your property’s amenities, and showcase your flexibility to meet displaced families’ needs.Highlight Insurance-Friendly Features: Emphasize features like flexible lease terms, utilities included, and a fully furnished setup to attract insurance placements.This approach has helped me successfully market to insurance companies.

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.  

The one that's short term and don't cost me a lot to initiate/originate.

I'm not sure if the program is still going on, but has definitely revitalized a lot of the area when it was once destined to follow the way of other older cities that are aging out of existence both in terms of people and property. 

I've seen a situation two years ago where a new landlord had trouble evicting a tenant who was constantly late on payments because the tenant argued that the late payment terms in the lease had not been honored since the start of the lease and couldnt be suddenly enforced because of this. 

What terms are they proposing?  

Might be a diamond on the rough if you can fix it up and then long-term rent.

Thanks, I'm looking to get into short term or long term rentals for starters.

It was a big project in terms of the amount of work it needed, I just ran out of time with my lender going through the garbage with the contractor, finding a new one, and finishing taking the longest. other than that I would've let it sit on the market to get closer to what I actually wanted for the property.