I took a 5 yr hiatus and not sure where to start again

[Azita S.]

I live in Portland OR and since the market has always been hot here, I decided to invest out of state.

I started investing in RE in 2013 and when the market was down I bought 2 SF in Peoria AZ and they are being managed by an amazing PM.  I've have 0 vacancies, no major repairs and they cash flow OK.  I don't remember the last time I talked to the PM. On 5th of each month I receive my direct deposit and the statements are loaded to the owner portal!  So totally hands off. 

Then in 2015 I bought SF home in Milwaukee WI, flipped it (long distance, never met with any contractors) and made $50K.  

Then I purchased 10 rental units in the inner city Milwaukee WI (5 duplexes) which were a huge mistake.  They quickly became money pits, high vacancy rate, lots of evictions, tenants trashed the units each time, dishonest PM's one after another, so the units never cash flowed and I tried for 3 years to unload them, but I was getting offers from local investors for less than what I paid for, not including all the repairs and upgrades.  I was on the phone constantly with PM's, city inspectors, tenants calling me directly, .... just a huge headache.  

Having to deal with these units, I decided to put a break on purchasing more since I felt like a total failure for a while. 

This summer, after working with an agent for 2+ years, I finally sold the Milwaukee units. I took a loss, but also learned invaluable lessons in RE investment. 

I've parked the $$ in a CD and have taken a break.  I own a non-RE business full time, have a young kid and a busy family life, so my next investment needs to be a no headache investment (buy and hold).  I'm self-employed, so my goal is to purchase enough rentals over time to have a nice retirement income. My goal is $150K in cash flow in order to retire. 

I'm back on the Bigger Pockets to start my research into the next chapter in RE investment. I'm interested in learning about possibly purchasing a vacation rental that we'll use ourselves and Airbnb it other times. or maybe couple of SF in AZ to have the same PM manage and be hands off.  

I consider myself a newbie and here to learn from the pros.