Have you identified seasonality for your region? 

I visited Cleveland years back, and to me the east side of the city was older, higher cap rates, and lower price per unit, but harder to manage.

We are very familiar with the area and have friends who live in the town, though we'd love to connect with anyone who has any experience or opinions on investing in this market... or experience doing furnished rentals in locations where there are peak seasons and offseasons.

Most likely a cash-out refinance won't be possible unless the loan amount is above 100k and the property is currently seasoned and rented.  

I am a pretty seasoned investor from Canada who wants to get into syndication seriously.

This was an off market deal that an older lady presented to me.

For all my seasoned flippers.

Also, be mindful of Portland's unique areas, such as Northeast Portland for duplexes and Southeast Portland for older houses.

Yes, the spring/summer season sees demand ramp up, but that doesn't mean a house listed in December won't sell.If you buy in October/November, chances are you won't be listing until January, anyways.If I had a house completed on, say, December 15th, I would likely sit on it through the holiday season before taking it to market, but I would talk to realtors.  

Of course, the virtual numbers that the tool spits out have to be validated "the old fashioned way" by confirming the assumptions the tool is making (comps for daily rental, occupancy, vacancy rate, seasonality, etc.)