Decided to buy it under the LLC for the liability protection.  

Many of us on the Front Range have switched to medium term (30+ days) as restrictions have increased.

If you are burned out you can rest for a very stragegic set period of time, ive done it twice where i switched w2 jobs and rested in between. once I gave myself a month and once a week or two. but I was very cautious not to stay idle and even on those days off I focused all my energy on resting, working out, eating perfectly cooked whole foods meals and studied for at least two hours a day dispite it being a break.

That way (theoretically, my entire portfolio of notes and equities are protected from inflation, and I still get a great current yield, about 14% on the note portfolio, and 8% plus appreciation On the equity part.

This protects the agent's time and lets them know you are serious.

Having it set up before my first RE investment purchase will give me the protection but is there a tax benefit one way or the other? 

Im thinking about switching to Section 8 for the guaranteed $$$$.

Real estate is commonly viewed as an inflation protection, so demand increases, which has an upward pressure on pricing. 

You will want to make sure you do not hold security deposits in Chicago, but instead switch to move in fees in the future.

Governor Ralph Northam signed a budget bill extending eviction protection until June 30, 2022.