I have always dreamed of owning and operating multifamily rental properties ever since I was a little kid.My mom has been in realestate ever since I could remember, everything from being a realtor, fix and flips, buy and holds, and long term rentals.

Consider different strategies like mid and short term rentals as I believe the Portland area would allow for success in both (although I have heard Portland proper is tough on STRs).Best of luck!

Also, I'd encourage you to think long term. 20-30 years from now, it won't matter if you bought your first property now or 3 years from now.'

Assuming these are for short-term loans, such as for flips, @Keith Groshans, you could do what we do and let the borrower keep the money and pay everything when they sell the property.

It seems to me though your short term objective is to get the HOA to take immediate action on the roof.

We all know houses historically go up in value over the long term.

Anyone speaking in "sure-thing / simple" terms, I call BS. 

I didn’t leave lol, but I was speaking in terms of the business in general.

These are what we call "A-class" markets—areas with strong fundamentals, high demand, and typically excellent long-term appreciation.

We use Appfolio for our long term, but I think you need a minimum of 100 units now, which is sad.