Hey @Levi Chuculate, Taking ownership draws from a fund have less to do with taxes (unless you would like to discuss the tax implications of receiving that income) and more to do with your operating agreement and bylaws.

Having a Pre-approval letter or better yet a loan commitment and a Banker to call and reassure the sellers agent you can close in 30 days or less also offers a huge advantage.In this market using a DPA is not a bad idea since rates are high and when they drop you simply refinance for a lower rate and payment. 

Conversely, I also know people who find communicating with guests and cleaners to be incredibly draining, they don't know the first thing about managing an STR nor does it particularly interest them, and they would rather spend their time making money in their main job rather than taking on a side hustle that they may not be able to do as effectively.

There is a larger market than just traveling nurses.

The whole process will take 2 hours start to finish and I am not even interested in billing them for the time, time is more valuable to me than money, and I just dont want us to have to take the time. 

Why would the basic structure of a subject to transaction be different in Illinois than it would in any other state?

If you sell a property in one year or less after owning it, the short-term capital gains is taxed as ordinary income, which could be as high as 37 percent.

Still learning the ropes here so mostly looking for any general pointers on the challenges investing in a different market than where you physically are comes with its own challenges.

I originally started working with my current brokerage specifically because the broker said she was more than willing to sponsor me later to get my own corporate license once I had the qualifications.

You don't have to do anything to your property, it will sell for higher than you bought it for last year.