You might want to touch base with my agent in Wilmington, @Rachel De Faut.

Quote from @Paul De Luca: @Michael MahungBrighton Park and Little Village have the highest concentration of residential units in 2-4 unit buildings in Chicago (70% and 71% respectively).

Wyoming and Delaware provide alot of anonymity. 

It is my belief that when scaling and growing your real estate business it is best to set up a structure such as a Series LLC or Delaware Statutory Trust to hold your assets.

I'm in Illinois, and plan on doing most of my business in Illinois, but have seen on the forums that I should consider filing in Wyoming, Nevada or Delaware for maximum protection.

Quote from @Paul De Luca: Quote from @Mana Ionescu: I contracted a company to manage and market the property.

In later years when the deductions are slim we always try and utilize the de minimissafe harbor model.

We deal with Escrow companies (Corner Escrow - Chirsty De La Torre) and title companies (First American - Noah Prestwood) as long as you have the correct documents, they can do the transaction for you. 

@Paul De Luca - I'd say the plan would be : - Get this northwoods place sold - Rent the cheapest studio I can find in an area I like, and start learning- Start with one building, be it a 2-flat, or a 4 unit, get it done in a year, perhaps on leverage seeing as I'd be keeping a gigantic nut of cash in case things go south.

Selling the lot next door to your rental property may 'de-value' it but it may also help to increase the vaule over-time as well.