Would you recommend anyone?! 

I’d recommend listening to the straight up Chicago investor podcast for local information, going to the variety of meetups that are in this great city, and meeting a lot of the people posting here. 

House Hacking a primary residence is the best way to generate wealth so I always recommend that as the next move. 

I would recommend targeting 30 day minimum rentals (Most associations are 90+), allowing 12+ rentals per year (most allow 1-3), and no in-person screening for tenants required.

Quote from @Brandon Croucier: 20% down is terrific on land.It’s a non income producing asset which has increased volatility, typically I see 65 LTV max on land as of late.Thank you Brandon!

Any recommendations are appreciated.

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

LOL Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

My Insurance Agent has strongly recommended that I put a Construction Agreement in place with my Contractor to shield me from liability, etc. 

Others recommend tools like Stessa or Buildium to track actual costs and project future expenses.