There are reputable companies out there, however, but I would shy away from any company that mentions turn-key.Long story short, real estate is very forgiving over time and these properties cash flow well and I was able to build a great team for future deals. 

As mentioned above, Portland has more restrictive rules than most of the state of Oregon.

A few of them also mentioned that they don't really expect this to affect the housing affordability in the county, but do believe that STRs can affect the quality and integrity of the neighborhoods in the county which they want to preserve.  

I noticed some of the reviewers mentioned how the area is up and coming so if the area is questionable that might be contributing to this.

As someone else mentioned, make sure you don’t go overboard with the updates.

Real estate investing has been a passion of mine for time with my mother also having invested early on where I likely have gotten the love and desire to follow similar foot steps.I have taken last 6 months to educate myself and currently own a single family home as primary residence and would like to expand to multi family properties (2-4 units) for additional stream of income, not to mention potential tax benefits for long-term investing.Based on current living situation, I have a fair amount of equity established in my primary residency along with having enough cash to either pay off house completely or use towards investing in a multi family property.Given that I'm the sole source of income for our household with my wife being the home maker for our two kids under 2, trying to weigh out risks with getting started now or perhaps waiting. 

As Elias mentioned above i think you're insurance costs will continue to rise and while the property may appreciate as well i don't think juice is worth the squeeze.

Congrats on finishing up the rehab, as others have mentioned, make sure to document your work.Keep the invoices handy.

Watched this one and kept waiting for the point you mentioned.  

This travel expense is not a business expense related to the property you already own until you have identified the next property you want to buy (once identified, costs are added to the basis mentioned above).