My brokerage has been tracking the data from the West Penn MLS for the past 2 years, and I would like to share some of the highlights so that we all have some hard facts to lean on when answering this question.

I think that you are on the right track thinking of paying off mortgages.

It also tracks who is in what house and all other resident info I might need, and is absolutely vital to our operation.Each of our houses has a live-in manager who, for free rent, ensures all residents are following a strict set of rules and guidelines that is enforced quantitatively with a points system to ensure objectivity and uniformity between managers and houses.  

Is it easy to creat an LLC on your own, or would it be wiser to hire someone to assist me?

If your short on cash or reserves you can always use a DPA program - Down Payment Assistance. 

If you're unsure about the shut-off process, contacting the city of Chicago for assistance or confirmation is a good idea.Has anyone here used a professional service to winterize their property, and if so, was it worth it?

For instance, I suspect vacancy might be a little higher based on the train tracks running directly behind the condo.

I appreciate your assistance and look forward in hearing from you.  

Hello,I'd like for someone who can assist me regarding the cancellation of my active membership that I paid for 2 weeks ago.

Good property management should be able to get you back on track.