Capacity and Tolerance. 1) Capacity: how many people can you comfortably fit in the property, is there room to add more, or add more value to the tenants to increase rent.2) Tolerance: How many people are you comfortable living with, if there are vacancies are you able to handle that.House hacking is an amazing path to homeownership, and a nice low barrier to entry into self managing your properties.

This is all despite the fact that they've made no improvements to the properties since acquiring them, and local property value indices only have about 15% appreciation for property values in the last 2 years for my area.

Use a quitclaim or warranty deed to transfer the title, and be prepared to pay Chicago’s transfer tax, calculated at $7.50 per $1,000 of the property’s fair market value.

Hello everyone, I am reviving this thread to gather a few contacts to whom I can bring value.

We have a high saturation of rentals that has caused the market to lose money. 

If the guest feels slighted, there is no fact checking service provided by AirBnB to confirm their claims, so it is up to you to let future guests know the level of professionalism you provide.If you are able, I would recommend editing your response to the 1-star review.

I have provided them a letter from my broker about the amount that can be used.

Sounds like you need to have a relationship with a couple of good contractors, 40k for vinyl siding sounds high, what was the material cost.  

BiggerPockets also has a calculator to analyze deals, and I highly recommend you start this as soon as possible, even if you are not ready to buy.

We would need to know your current operating expenses (and rent) to be able to provide any suggestions.