A little anxiety is fine and helpful but honestly you don't need a coach for what you are proposing. 

Is the $10k for Engineering and Design a one time thing or a recurring expense?

Once i get a list of targeted property owners names, physical and site addresses etc... what would be a good service to use  where I can upload my list and have all my postcard sent out with a schedule for recurring mail?

We were mistakenly given an upstairs unit one time immediately after I had a baby (she was like two weeks old, and our fourth child so we had an 18mo also, and the concrete stairs gave me the absolute worst anxiety) so I agree that a three story walkup won’t be agreeable to her after a few months and she might want to leave anyway. 

I would say if you are a beginner, the geographic distance is probably going to cause you some anxiety over the years. 

—as security for a loan, the borrower has a contingent liability.The lender is not required to include this contingent liability as part of the borrower's recurring monthly debt obligations provided the lender obtains a copy of the applicable loan instrumentthat shows the borrower's financial asset as collateral for the loan.

You mentioned "not being able to sleep at night" due to anxiety from borrowed money.

I’m not necessarily trying to have immediate cash flow with this, I just have some anxiety knowing that the cities I’m considering buying in will continue to get more expensive and I already have enough for a downpayment so it feels like a waste to not buy sooner than later.

It seems insane to me, as my monthly recurring expenses are $375 before food, & $110 of that is Public Storage, so it's $265 once I move in.How strict is this 3x rule (OF THUMB)?

When we have had to travel the bank has held the checks and deposited them on the first themselves.Electronic payment requires action from the tenant in that they have to either initiate a one time payment each month on the first or they have to schedule a recurring payment for the first.