While on this journey I would love to start going to meetups or finding like minded individuals related to investing in real estate specifically in my area.

There is a roofing guy owed money but he isn't going to lien us because he is owed from other jobs from this builder so is suing him.

With a virtual number, I will always know the call is related to my STR or my other business because the business number pops up when a call comes in.

It's landlord friendly and still relatively affordable compared to other hot markets around the country.

Talk to your parents, or another trusted relative, about co-signing a mortgage with you.

If you have to pay the relative half of the equity we need to know how much equity exists.

It's on the far NW side and has inventory in that price range, but consider that taxes are relatively high in Elgin VS most suburbs.   

If you have a nice house and you are in a busy real estate market you can let a relative or friend list your house without loosing too much, if they are good workers.

  (1) It sounds like your LLC is a separate tax filer, but the issue you may run into is that the IRS makes it tricky to buy from "related persons" under IRC 267(b) (a category that includes business entities) in a 1031 exchange. 

It depends on what the list price is relative to the fair market value, how much competition there is and what the numbers look like.