I think the height requirements in Chicago are 7'6" and we're right on the edge of that. 

I understand that starting out, depending on how fast you want to build your portfolio, you could spend a lot of time at it.For those with established investment portfolios, how much time is required to maintain it?

"light clean out required once tenant moves out." 

One of my buy box requirements is the house needs to cashflow at least $500 per month or I am not buying it. 

If you don't have a key, change the doorknob to an appropriate interior knob that doesn't require a key.I provide my tenants with keys to all doors.

Your $80K HELOC can serve as the down payment, as most lenders require 20%-25% of total project costs upfront.

The deed transfers to the trust without triggering due on sale and that is the only item requiring recording in the process.  

A DSCR loan is going to require more down, have high fees at closing, a higher interest rate, a pre-payment penalty, and will require you to have cash reserves that you likely don't have at the moment.

Dodd Frank corrects this by requiring the price be supported by an appraisal or some  basis. 

We've sold 65+ homes and the biggest request we get from our Buyers is help with closing costs.Most of our deals we're providing anywhere between $5K-$10K to help Buyers offset the cash requirement to purchase a home.Even in today’s "high" interest rate environment, many Buyers prioritize closing cost assistance over an interest rate buydown.