Considering Owner Occupancy Chicago

[Shaun McPeck]

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!