I have no social sphere or contacts family or friends in Oregon (I don’t know anyone besides my fiancée).Goals: continue to have flexible schedule while enjoying what I do (selling real estate) and making good money.

Hey Bree,It's fantastic to see your excitement... it reminds me of a friend of mine who was in your shoes not too long ago.

I would advise finding an investor friendly realtor when you choose a market.

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.

You have received some great recommendations and if you are yet to decide on an Investor friendly to work with, you can send me a DM and see if we are a good fit.I do provide free mentorship and a lot of free resources and connections to anyone I work with especially beginners like you. 

Borrowed money from friends and family to pay cash for the property as the bank would not finance it until it had been remodeled, made livable, and brought up to code.

rent out all the bedrooms to your friends. 

it is not user friendly at all.

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. 

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?