Hey guys, wow, thank you so much for the abundance of replies. I read through so many different perspectives and experiences on property management and it was truly educational. There were a few common threads:
1. It would best for me to start my real estate investing career managing my own properties to learn the ins and outs of the business so I can better choose a property management company in the future.
2. When it comes to finding the right property management company, my best bet would be to ask other investors, look up reviews, certifications, portfolios etc. before making any decisions regardless of company size, name power etc.
3. Property management won't necessarily be needed for me in the first 5-10 units as I plan on sticking in the Portland metro area if I can. However, once I get past 10 units PM will be something that I'll strongly consider (but who knows, I could end up creating systems to manage the properties effectively myself).
@Thomas S. makes an important point: even if you have property management you still have to manage your managers. However, I will say that this sounds much more preferable to me than dealing with tenants / maintenance / listings etc. On the flip side, I've heard from some that managing properties really isn't that much work overall. Still, for me personally, because I run a successful business in a completely different industry that keeps me plenty busy, I think PM is something I will almost certainly utilize.
You're right there's no such thing as completely passive investing... but I want to get as close to that as possible with my investments. First, it seems to me the best way to learn is to get my hands dirty, buy and manage a few or more properties and see how I feel after everything I've learned. Like I said, PM is still a strong possibility, but you guys have given me a lot of perspectives to consider. This thread has pretty much made me certain that I'll wait on PM until I've actually got some units and preferably a year or more of experience managing properties.
Absolutely determined to take action in 2017. Right now I'm still renting, so I plan on buying a single or multi family home and house hacking/BRRRing it then starting to buy other properties from there. I'm going to try to buy at least a few investment properties in 2017 and really start going at it. The rest of 2016 is dedicated to education. Thanks again for your thoughts here, guys, truly helpful.