Completed high value renovations to boost market value - new roof, etc., What was the outcome?

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. 

Acquiring knowledge boosts confidence in our convictions and enables you to invest even in the face of uncertainty.

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.

Your first property could be doing well to start because of the boost Airbnb is giving the listing, and there is a need for a STR.

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

So I'd recommend thinking about who you want in the property and then determining the bed configurations and numberthank you so much, great things to think about: i hear others echo your sentiment not to count the sleeper sofa as a bed as much as a 'bonus' if people ask, so i appreciate this insight. i thought it might be okay, as it's memory foam with a topper, but ultimately i agree that it's not where i'd want to sleep.