My suggestion would be to get an investor friendly agent who knows a few local markets and have them guide you in the right direction.

You won't have the options that you have here in Austin, mainly because Portland is Tenant Friendly City and Pfugetville is Landlord friendly.  

I rented out the additional bedrooms to friends and family, charging them well below market, and sold when it was time for my wife and I to start our own adventures.

I am looking for a solid real estate agent and eventually will need a home inspector, possible property manager/etc. in regards to the process.I have a few family friends which I am blessed to have mentored me the past few years in this field and I am determined/diligent to learn and grow. 

I am betting your gonna find a lot more friendly amicable persons than shut doors. 

rent out all the bedrooms to your friends. 

Just google the following: - special assessment - zombie condos - Florida condos (look for recent news)Since you are not living near the properties anyways, why not look in a landlord friendly state where the purchase prices are lower?

I'm up at Lake Tahoe in the basin and there are many CA investors that have been investing in Reno, NV because of the low taxes, landlord friendly, and only 30 minutes from Truckee.

Your job will be to find an investor-friendly brokerage willing to teach.

Low barrier to entry, low taxes, landlord friendly, and areas that appreciate + cash flow.