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?

[Eric M.]

Well, first you should be using an agent but it does also make sense not to considering your strategy. It sounds like you are not against buying from the MLS (where the agent would get paid) but you are also hoping to widen your net by buying off market (where the agent probably would not get paid). My guess is if you were upfront with the agent and told them...if you bring me a listed deal I will buy through you, but I will also continue to look off-market on my own...many would be cool with it. Just don't make us do a whole lot of your leg work on the off market stuff.

The first thing to do is scour AirBnb for listings and begin to map addresses. This will help identify buildings. Of course, some listings will be trying to be on the down low in buildings where it is not allowed. So you need to check. Once you have found potential buildings, search for listings. In the MLS listings (of current or old listings) there will generally be a phone number for the management company. Call them to confirm the rules.

As for contacting owners, it is all public record and you can skip trace and get info to either call or mail a letter.

Just remember, if STR is your sole strategy, buildings change rules at the drop of a hat.

Also google Prohibited Housing List. These are the buildings which have reported to the city that STR are NOT allowed. Doesn't mean all the other buildings ARE allowed.