tl;dr: Total noobs looking to house hack in a Chicago north side hood.

The sell of that property was for 415k total.

The properties appraise for 75k and 100k, for a total of 175,000, and my bank just gave me a check for 50k to refi the first property. 

In this scenario, you put down 30K on 5 properties and each property cash flows before mortgage payments $800 and each property will have a payment around $700 per month (I am assuming you will end up with 5% loans and 25 year amortizations which pretty typical on investment property in my experience at the moment) leaving cash flow of a total of $500 per month, significantly less than the $800 or so you got for buying 1 for cash however you will also be paying down the mortgages at a rate of about $200 per house per month which is another $1000 per month in potential gains. 

If you look at the first picture there is a Vacancy & Credit Allowance just under the Total Gross Income and I've accounted for a 10% loss.

In my calculation, it seems that the loan points apply only to the “Acquisiton Loan Amount” rather than the “Total Loan Amount” - I was wondering if this is true, and if so, why?

Say you have an adjustment worth $50,000 with Form 3115 and you're paying taxes quarterly and your total annual tax bill is $100,000 with $25,000 due per quarter.

I totally agree we everyone regarding the low rents. 

With delayed financing, will banks go off market value for ARV, or off the total cash invested (purchase + rehab)?

I currently have a year and a half total with the same company.