I wished you were near me......this is definitely something that id be interested in for sure

In a better market you might be able to use those things to get a better deal on commercial insurance but in the current market there won't be flexibility.On personal policies/1-4 unit rental dwelling policies there won't be any flexibility whatsoever unless it's something the company already has built into their guidelines/pricing.

Ideally, I want something I can confidently show to potential investors that includes all the key metrics they and I would need to consider when evaluating a property.

Could you sell or 1031 exchange a dud and use the funds to buy something else?

Just want to get going because I believe this is something I would be good atI am looking to start by wholesaling in the Chicago-land area and I know you need a RE license for that which I am currently debating on.

The sooner you start the better. 1)look at other markets. 2) once you’ve established what you need, go see a couple of mortgage brokers and discuss your situation. 3)take action - buy something sooner rather than later. good luck, if you have questions, I’m happy to help. 

My lender packaged and sold my mortgage, and when I called the new servicer to inquire about a HELOC/ Home Equity Loan they told me I wasn't eligible because of my short ownership duration.I am planning to pay for most of the improvements with cash I have on hand from my W2 job, but I want to get something set up in case of an emergency repair/ use towards other investment opportunities.

I wouldn't go into something already knowing it was illegal, you are just asking for trouble.Just because other people are getting away with it currently doesn't mean they won't get shut down in the near future.

If you need a loan for EMD, then what are you doing buying something?

Unless there's a tripping hazard or something like that you should be fine (and even in such cases, your insurance should cover it although they might force you to address the tripping hazard).