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.

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

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 can also document that I have over 1,000 plus real estate transactions as an agent and an investor.I had two transactions that they just kept lying and telling me and selling me you will have CTC in a week or less, From each of those points it was more than 60 days.I begged loan officer and processor to be truthful.Their failure to close in a timely manner cost me dearly.

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. 

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

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.

I am BP's Premiere Featured Agent for the WMass area.