How would I go about this? 

@Jason Weidmann what do you think of every agent responding telling you to go, go, go!

I’ve done 1 rental property and sold it to gain capital and did 1 flip that didn’t go so well so not 100% experienced to say the least.

I have used united granitethey are in willow brook- more south west burbs but i’m sure he would travel. my guy is Oswaldo- DM me for contactyou gotta go to the warehouse to pic out your stone and he doesn’t do demohe charges $200 to provide the sink which is a deal i highly recommend

A lot of things are going right for you.

The first half of the year will be slow going.

I just spoke with my insurance agent and he mentioned that I am unable to hold a policy on a property that I do not own (Since deed will be transferred, I can not hold an insurance policy on the property), so how do I go about fulfilling my lenders insurance requirements?

if you're W2 and full-time, hourly or salary, you should be able to go off your pay stubs for qualifying.

In his recent project he was able to build it for under 190k - 1 bed 1 bath unit with about 450sqft and it is going to rent for $1800/m. 

.- The inspections are only 5 years, but tenants are not likely to take care of them home as well as you, and refurbishing hardwood, lath and plaster, and anything else is going to be much more expensive than the typical Landlord special (white paint, and grey LVP)It will all come down to making your numbers work.