Rentals or Airbnb in Portland?

[Justin S.]

It's time to get my first investment property. My lease is up in four months and I hope to find something before then that I could House Hack. I live in Portland, that's a tough place to find an affordable duplex, so I have been searching a little outside the area, but still close enough to work. I have a friend Real Estate Agent who is also searching for rental properties of her own, is that bad? How can she help me if she is looking out for herself as well? What if I show her a property I like and she wants it? Another similar option is Airbnb. I currently live in condo type apartments. An investor subleases about 8 apartments in the building and uses them as short term rentals. I talked to the lady who cleans the properties and she said they charge $200 a night. They are making bank!!! I'm considering getting into this. I would love to meet someone in my area who is already doing this and can help me understand my different options and any problems I may face. I have read and listened to podcasts about it, but knowing someone who actually does it would give me more confidence. Thanks for your responses. Any ideas or advice is welcome.