All Forum Posts by: Shaun McPeck

@Lance Blight - I'd recommend Avondale which is just north of Logan.  That is where I live and am basically doing the exact same thing you're talking about here.  I think you'll see better price points in Avondale than you'll see in Logan.

On a good month, Airbnb covers the entire mortgage (and more) on my 2 unit building. I haven't been doing it a full year yet, so I don't have a ton of data.  But I'd be happy to discuss with you and talk about the neighborhood.

Best of luck!

+1 @Stephen Brieloff for his mention of BeyondPricing.  A very cool system.

@Robert Los

I've not yet dealt with a rejection or appeal, so I'm not sure how that works.  I'm sure I'll run into it at some point and be able to provide details on my experience.

@Robert Los

When you sign-up on Airbnb and list your property, they automatically submit your application to the City.

I'm very interested in this topic as I own a 2 unit building and the rules in place prevent me from renting the unit on Airbnb that is not my primary residence.

I'd be curious if other investors who are having this problem would want to band together and create an alternative that, as far as I can tell, would sidestep the law as it is written. Getting a lawyer's take would definitely be a plus, of course.

It all hinges on the fact that the ordinance applies when using what they call an "intermediary" to list your rental online. An intermediary is defined as listing service that collects "a fee or compensation."

So I'm thinking of we created a Chicago only clone and didn't collect fees for listings, it wouldn't meet the definition of an intermediary.

I have the technical chops to setup and host a website for this purpose. There are companies out there who have already created the software that we could jointly purchase.

Any takers?

Sorry to maybe hijack your thread, Ivy. I'd be happy to chat more about details on the law as I've read up on it a good bit. Shoot me a message if you'd like.

Hello.

I'm going to load this introduction with details on what brought me here and probably weave tons of questions throughout.

I currently rent, but I've been dreaming a bit lately and looking at 3 flats here in Chicago. Part of this dreaming isn't so crazy. I do expect a decent windfall of assets in 3-5 years when my employer IPOs. I really like the idea of the 3 flat because I think rent would more than pay for the mortgage.

The more I look, however, the more I get excited by certain properties. This makes me start thinking about the possibility of biting the bullet before the windfall comes to be.

Some things to mention and questions:

• I do have a short sale on my record (over 4 years ago)
• If I can end up putting 40-50%, does a 15 year mortgage make any sense?
• With the short sale, how much will I likely have to put down?
• Any comments on the plan of working things as an owner occupied building?
• Would you avoid committing too much of the windfall?
• Would you start things before the windfall and maybe go for a cheaper 2 flat even though rent wouldn't cover the mortgage?
• Should I buy the property as a business entity and rent from myself?

I expect a lot of answers with links to existing posts/resources. That's ok. 😀 I imagine, also, that there may be extra questions about my situation. One item worth mentioning is that I'm not overly concerned about income needs - but, of course, I want to make financially smart/sound decisions. I do have a slight concern about the short sale on my record.

Apologies up front for the big dump of questions as an intro, but I didn't want to risk muddying a different area of the forum with this broad stroke of a post. If I should have directed some of this content elsewhere, please educate me.

 Cheers!