Ultimately no one has more to gain or lose with the deal than you so you are responsible for all decisions that are made.

Ultimately allowing you to automate the scheduling of your field-work. 

Therefore, if you choose to sell the subsequent property later on, you will ultimately be responsible for paying the taxes.I would retain ownership of the property, continuing to generate rental income, while leveraging a second position loan to acquire additional investment properties.

As a conservative investor I might look at 50-10 deals a month and ultimately choose 2-5 a year. 

While many people my age are barely surviving, or still living at home, I took huge risks, saved diligently, read everything I could get my hands on.

Standalone brick and mortars like compass are the ones that are burning through money and taking it from the agent and customer it is very hard for compass to survive in those environment, as company like as big as amazon or apple move to hybrid work environment, the compass failed to grasp the spirit hence their transaction cost is so high.

@Scott Trench I think human nature makes it is easier for people to be more pessimistic than optimistic (survival bias). 

It turns out that the tenant had not paid the rent in November and December (and ultimately January too), because the previous owner allowed the home to fail 2 section 8 inspections before I purchased the property.

I'm in Chicagoland, but south burbs.I read and researched a lot, but ultimately I got started by following the steps in this book: The Weekend Millionaire's Secrets to Investing in Real Estate: How to Become Wealthy in Your Spare Time https://a.co/d/gLYA4SjThey give you the step by step.

But, ultimately, you're right - strong appreciation can justify a cashflow negative investment in some cases.