Should I go ahead and try to buy a house now, or should I wait?

Go ahead and tell us who you are dealing with so others will be forewarned. 

However, this is a small, 1080sqft 3/2 and the kitchen, laundry and bathrooms are all along a straight line path.

You have an exciting journey ahead.

Personally Id just wait another year and then do it again, Once you move and get the additional income from the original then go ahead and do the heloc 6-12 months after to get your third property.

I would go ahead and get your own mortgage at 700k and then have him loan you the remaining amount as a personal loan over 1-5 years.

If we had just bought things in March of this year we would be way ahead. 

It's good you're thinking ahead!

I recently started listening to podcast started by I believe @Tom Shallcross (please correct me if I am wrong) called "Straight Up Chicago Investor" where they speak with investors on where they have had their success etc. in the Chicagoland area. 

Hi @Reba Vera - normally management companies should take some time with you over the phone or email to go ahead and explain the terms of their contracts and answer any questions you may have.