Born again real estate investor

[Keith K.]

Hi, I am new to the Bigger Pockets community, but not new to REI. First, sorry if this is a long post, but I've been really into writing lately and hope you can bare with me and hope you may see some of yourself in my story and can provide feedback.

I had my first 'go' at it over ten years ago after reading Rich Dad Poor Dad. That book solidified thoughts I had all along and, as a result, found a property and purchased it directly from the owner at a good price. My vision for the property was either flip, rent, or hybrid.

Unfortunately, the investment took a long term detour when my source of funding decided they had a different vision for the property (nice place on the Oregon coast) and wanted to keep it in the family forever. Dreams of passive income bliss became a 9 year drain on our bank account. During that time, I decided that if this is how REI was, then I didn't want any part of it.

I still obsessed over passive income streams and spent those 9 years trying anything and everything including the stock market, online marketing, and even mobile app development. While I learned a lot of new skills, I hadn't really chipped away at my passive income goal.

Having tried 'everything' (okay not really, but it feels like it), I went on a long hike alone on a plateau above Lake Billy Chinook in central Oregon. Long hikes are always good as I get several hours to talk to myself and inevitably learn something. The Oregon coast property is starting to make income as a vacation rental, not cashflow, but yes -- income. And it's a start. In fact, this little realization transported me back through all the 9 years of trials and failures. I realized that none of these are going to get me to my goal, but REI could if I approached it with more care, patience, and with a better plan.

That's where I am today.  I am still working on my plan, but likely to focus on buy and hold for making nice rentals in my community (Portland, Oregon); flips and simply finding deals for others may also be an option if the opportunities present themselves.  Partnership is also something I am seriously considering because of the 1+1=3 effect and that making your friends wealthy is as satisfying as making yourself wealthy.

I am interested to hear your thoughts.  Questions currently rolling around in my head:

-Property management role? I would like to keep REI as passive income as possible so would like to hire out property management. However, I understand that you must first know how to do things you will eventually hire others to do. Is it possible that I could hire property management out from the start, as long as I took extra care in observing their performance in the beginning (almost like a probationary period). Or, is learning property management first-hand absolutely essential for success in REI buy and hold strategy?

-How to involve a spouse who doesn't share the passive income vision, but does like 'looking at houses'.?  I don't think I really need to explain this one.  

 Thanks for letting me into the Bigger Pockets community.  

Keith from Portland, Oregon.