The biggest challenge (and this is what I had to learn the hard way) will be to overcome the decades-long stigma that has plagued the neighborhood and get prospective tenants to sign on.

You couldn't say that you buy "ugly houses" but you could create a unique brand for yourself.

My challenge is using what I have been taught to determine the offer amount.

As an investor, are you looking for anything unique in an inspector that an owner occupant wouldn't be concerned with?

The reason you are getting what seems to be a lot of misinformation is that this is an extremely complicated subject and the advice you receive depends on a number of circumstances that are unique to you and what you are trying to do.

Now that my kids are older, I want to be professional about it, have fun(meet challenges), and use it as a way to achieve financial independence.

Unfortunately, the real estate industry is hardly unique in convincing people to spend money.

Other success/challenge stories appreciated!

On 1031's all the exchange companies I talk to say that 1 year is generally held by the IRS to be viable according to case law and rulings for holding for investment purposes.Anything under a year and the IRS is aggressive to challenge the 1031.

I would like to do something like this in an effort to ascertain an off grid IL rare unique property.