I get the desire to own outside of Chicago proper, but instead of going to another state altogether, why not invest in one of the burbs?

Like Jake Baker suggested, keep good records and have a dedicated bank account for your property, properly separating personal and business expenses.

Learn the ins and outs of fit and finish, proper preparation, proper installation, rough in locations & MEP details... thinking 10 steps ahead on everything.

Insurance is going to protect you financially from lawsuits, damages, total losses, and other scenarios we can't even begin to imagine until it actually happens.You'll want to have a broker you can work with and trust that will make sure you're properly protected in the event of a loss.

I have a few brand new homes popping out of the ground in Canby Oregon.. msut of Portland proper is very old the new builds tend to be skinnies or expensive . 

that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

Location & expertise in manufacture rehab How did you find this deal and how did you negotiate it?

I think too many people get into this and struggle for too long before realizing that they not been properly trained and potentially could have dramatically shortened the learning curve.   

To properly evaluate the condition and determine the cost of renovations, always have a professional inspection done before making a purchase.4.

And actually, if you structure things properly you shouldn't have to worry about the tax implications at all.