Should I find a local agent or use a lawer?

One of my friend happens to be a RE agent, landlord and a property manager himself and he seems to feel that as long as she pays rent on time and does not create nuisance, not to worry much and just keep do a quarterly property inspection.

Like Agents who say they are in the million dollar club.. well when houses were 50k each that was something you know 30 plus years ago..

If you have a real estate agent in your market that can help, ask them to look up any old listings on the property.  

I'm an agent and investor and about 80% of my buyer clients all house hack.

You'll want to have an insurance agent familiar with rentals since a lot of the extras on your coverage that you will want, the average insurance agent won't know to give you. 

Plus, if you'd like to connect and talk marketing/sales happy to do coffee or something.Also, there are tons of Facebook groups for Chicago real estate.Lastly, just doing some 1:1 networking with lenders, agents, and architects is something we focus heavily on.

I remember going to a mortgage closing on a personal home decades ago and the closing agent pushed the 3 inch stack of papers over for signing and said:"This all says...

I'd also recommend finding an investor-focused agent in that market, sharing with them your buy criteria, and then having them set you up with an email list for properties that get listed. 

While it will likely give you more confidence and answer a lot of questions, I would say that talking to a seasoned investor, or even agent that works with investors, is a way better idea than spending 8K on something that you don't know too much about, especially before your first deal is done.