My advice would he to find a local attorney that is also barred in IN (which should be prevalent because you're in Chicago) and a local accountant you trust.

It's the same as buying out of state, but just a little added fear since it's across an ocean.

Like to the point where there isn't any fear anymore because you know this is your calling.

My biggest fear is not having enough money out of pocket to cover downpayment, closing cost and etc.  

Those with a lot of hustle will do better, but the thing that stops most agents in their tracks is the fear of making prospecting phone calls.  

It's very prevalent when you see many houses (almost tear downs, but livable) built in the 1940's with numerous code violations and right next to them are new builds in 2017 or 2018 while the appraised lot values are doubling each year.

Fear that she will hang up on me and lose $$ due to my lack of wording makes me paralyzed to act!

A large portion of this is fear. 

I have been putting off my career out of fear.

Create that specific avatar. age, height, eye color, hobbies, work, children, married, goals, fears... once you know this, you can then network where they hangout and build relationships with these people so when you have a great opportunity you can present it to them and let them decide if they trust you and like you enough to give you their money...i buy multyfamily around the country using OPM. i raise capital for everything. the down payment, the inspection reports, lender fees and equity.. i dont use my own money. that's the beauty of real estate.. start asking yourself, what funds do i need and who can help me get it..?