I have liquidity from the previous business to invest and hopefully kick start this endeavor.Biggest challenge - I don't know this industry, I am coming from a completely opposite industry in the technology field.What I have, I think, in my favor, are colleagues from the RE industry with experience in both traditional RE sales (agent/buy/sell) but also experience in the REI side (one owning about 70+ properties and the other owning about 25 properties, both using their properties for passive cashflow)With an engineering/analytical background, my greatest fear right now is the unknown and I am trying to shore up that experience through reading and listening to others, but as I have already discovered, its like taking a drink from the fire hose - way more knowledge than I can consume in a short period of time.Questions I would pose to anyone interesting in providing some feedback -- Best way to look for that first opportunity?  

I plan on buying 2-3 properties, so it's going to be a challenge!

, ... even verbally sparring with the occasional challenger is all social exercise for me.I still say the wrong thing quite often, or say something folks don't understand.

However, there is one tenant we inherited who accounts for 80% of our maintenance calls, most of which we suspect are caused but her two young children.

In Oregon, I’ll be submitting myself to 150 hours of education, so that’s going to be a challenge to say the least.

I do Agree with not using the words "Always" & "Never"   As I was told that in Marriage Class when discussing situations with my wife or children....  

They need to sell.Here's the challenge I bet you'll face. 

What I love about real estate is that it is intellectually challenging because you can never know it all; always more to learn!

So that would have been very challenging with an occupied unit if you plan to do that, but perhaps your market is so hot, that fix up may not be required.

The place where you will have a challenge is the transfer tax statement document.