One of the tings you need to learn is that if you dont want to be a "finance person" then property management or real estate in general is not the career for you, because it it all boils down to numbers and if you think you can wing it without understanding finances then you wont make it in real estate.

I have already secured renters and am very excited to get started.Regarding the Chicago market, I have come to understand that there is an abundance of multi-family properties, but it is important to note the property taxes outside the city limits can be very high.

Calculating potential rental cash flow involves considering factors such as property taxes, maintenance costs, and potential rental income.Consultation with a local real estate expert can provide insights into market trends and help you navigate the specifics of converting your home to a rental property.Additionally, understanding the current market value of your property will contribute to a more accurate assessment of potential equity gains in the future.Hope this helps!

I understand 100%.

Understand the relationship between cheap, inexpensive properties in crappy neighborhoods that are so attractive to new investors because of their affordability and the poor quality of tenants that such properties bring who can damage your property and stop paying rent turning your paper profits into losses.

I almost don't understand it.

Any details would help us understand how booking.com works with claims... 

I'm also quite knowledgeable about real estate investing through YouTube, although I understand that it can be like Googling why your knee hurts - there's a lot of information out there, and it's not all reliable.

As long as you TRULY understand this will you be able to have a chance at success...

I understand the protection it provides, but there has to be a simplified way of doing this.