I’d love to have real estate provide some financial freedom/flexibility and create a portfolio that I could eventually get my kids involved with and pass down to them, but I end up feeling frozen/stuck based on the factors above. 

She realizes after we paid her and contractors she hired over $5,000 to get it painted , cleaned etc that we are out of money and she agreed to not charge us anymore but is still somewhat helping us and showing to potential renters .We have discussed different terms as I told her from her on out we can’t afford the monthly rate anymore .  

It was the owner of the house and a couple of neighborhood teens who handled the demo and clean up.

@Zach RumfieldEstimating an ARV involves using public sales data, subscription services, local tax assessor's website, real estate agents, CMA tools, and local appraisers.

Meanwhile our local properties were having increased cash flow without the effort involved with 2 hurricanes. 

But get an LLC and rent from it personally...any cleaning expenses, paying your mortgage etc. come from the LLC's bank account, any outside money that you need to fund the account will be a capital contribution and then you will be able to do cost seg on that property.

This strategy involves having a third-party entity hold the replacement property while you complete the sale of your relinquished property.

I will say we generally have no trouble keeping ours full and we focus on having nice, clean, safe spaces.

If anyone is open to sharing advice, offering guidance, or involving me in hands-on work that could enhance my learning, I would be very grateful for the opportunity.

I don't know how IL laws are but I think in most places a local municipality can only charge a fee to provide a service and the cost of the fee must roughly correspond to the work involved in providing the service.