STRs: Buying Without an Agent

[Jenna G.]

I am a first time buyer in the Chicago area. Most HOAs make it difficult for buyers to rent out as a STR downtown Chicago, but I have found a building downtown that will allow me to rent on Airbnb, etc. The unit came on the market for a few months at $300k, and is now off the market without a sale. Two questions:

1) Any tips for how to find more of these units? Is the only way to find Airbnb eligible buildings to call each HOA?

2) I'm considering trying to contact the owners in this building to see if anyone else has considered selling. I've heard some investors do this on the BPPodcast, but wondering if this is an okay route for a first timer. Is it okay to do this, and if so, should I drop off letters at the door or mail letters to each unit?