I currently am a realtor in Illinois and I operate my business under a LLC.

This is my business since 2011.

It's a business so the rents will be the main income and subtract expenses including savings.  

Not a "hey let's read everything" journey, no, pick a strategy, get THAT highly rated "how-to" book. 

Does it have a second strategy if you wanted to make it short term?

No offense, but you want to act like a company or business to make money, but you don't want to take responsibility like a company or business.

You can make numbers work in the area you will need more capital and a good strategy. 

SOFTWARES/TOOLS WE USE:Quickbooks (just changed from Stesa) - AccountingGmail / Google Drive - I create an email for the business and use this as a shared drive for all of my rental documentation.

my business partner and I have decided to go in on investing together!

If you're the type of investor to leave lucrative vacation rental investment to luck, then this post is not for you..It is intended for those that are looking for a fool proof strategy and tips to finding, assessing and buying an STR in the mid to near term. 1.