If the seller has children or a spouse that will inherit the property when they die, the tax basis in the property will step up to the current value for the heirs.

Sounds like you've got some solid goals with actionable steps thought out on how you'll achieve them.Make sure to keep everyone updated on your progress, and feel free to reach out if you ever have any questions or need anything!

I am currently pursuing wholesaling in Chicago and just recently began.

At a high level, I am trying to determine whether a refi makes sense/is possible given my current situation, or if I should pursue conventional/fha mix with remaining VA entitlement. 

I wrote a BiggerPockets post on how to find comps and adjust them for that first step of finding ARV that might be helpful: https://www.biggerpockets.com/blogs/8814/68395-how-to-find-real-estate-comps-and-calculate-after-repair-valueIs there any other part of flipping that is holding you back from getting closer to your first deal?

We have taken all the steps in creating our real estate investment group and we just got approved for our first property.

I think back to my best days at the court house steps and that was 2004.. this is not Canada.. 

If you are looking for true auction homes - you need to find the advertisements for them and then show up at the courthouse steps the day they go to auction. 

Congrats on taking that first step to put your stamp on this community!

Unless the property is on a waterway or lake, I would look for another property.BUT, its a different story when you can step out back, lower your boat.