You need to understand that we are only obligated to whats in contract.

You understand some of the basic concepts, but also have some giant holes in your plan.

Quote from @Max Martynenko: Thanks for your understanding and sense of humor!

It is my understanding that gifting a property does nothing to step up basis as the capital gains would follow the gift. 

It helped me to do more research and better understand that I’d like to buy property elsewhere and rent that out, rather than renting my current property.

Thus, my main goal joining this forum is to try to gain confidence in the decision to get into real estate investment and better understand the risks that I may not be considering due to my lack of experience in the field.

Verifying last 2 years of rental history and income extremely important to find the “best of the worst”.Make sure you understand the Class of properties you are looking at and the corresponding results to expect.The City of Detroit has 183 Neighborhoods we’ve analyzed.DM us if you’d like to discuss this logical approach in greater detail!

Understanding that you're in New York and the laws are leaned to be tenant friendly, I would still say this is the best way to go about it as a new investor.

A straightforward way to estimate value is by looking at the price per square foot and using that to calculate your property's worth.In situations like this, it's worth spending a couple of hours yourself to get a solid understanding of the market.

Now, take some time to understand the local market.