They are snoozers that in my opinion would not be the first choice of a sophisticated investor. 

@JT StanfordTo start buying real estate in Chicago, as a first-time homebuyers you should your budget, look at loan choices, talk to a loan broker, check out places like Woodlawn and Greater Grand Crossing, and choose a property type (duplex, triplex, or multi-unit), look at move-in ready homes, work with a local real estate agent, and plan for the future.

If someone wants to be within a specific market, the conditions within that market may wind up making that choice for them.

But here is my first option:My recommendation involves thoroughly analyzing the seller's financial and tax situation to determine whether receiving a lump sum payment is more beneficial than periodic payments.

Second question, I have an umbrella policy, is that a good choice?  

If you're looking for more of an appreciation/forced equity play, Portland can be beneficial, especially if you consider house hacking.Lastly, connecting with a local real estate agent who specializes in multifamily properties can provide invaluable insights and help you find the right deals.

Ben's reply has good info on the deductibility of having a mortgage on your primary residence, and how it's only really beneficial if the interest and along with your other itemized deductions is more than your standard deduction. 

Basically, if you are committed to this investment thing, you will need to make some uncomfortable/hard choices to eliminate the credit card debt and lower your monthly debt.Once that goal is complete, you can begin practicing habits to live below your means and start building up your savings. 

A new survey might be beneficial.

May be beneficial to join prop radar and refine search options to search this way.