Possibly do not even yet own their primary home?

Quote from @Anne Christensen: I'm just starting my real estate adventure, but I do rent my basement on my primary home. 

Does anyone have any tips/ advice to help make sure my property will appraise for what I planned on based on my rehab?

I think both of your strategies have merit, but here’s my take based on what you’ve laid out.Moving to a rent-stabilized apartment and renting out your condo as a mid-term rental could be a smart pivot, especially with its location near a hospital and LGA.

Need some advice.I do some small private money lending to home flippers.

The local property will give you practical management experience.You might do better buying a REIT if you are planning to buy single properties far from home.

Are they commission based, flat fee?

In some cases, after running the numbers, I’ve even faced potential negative returns, causing me to miss out on promising deals here in South Florida.That brings me to my question: I currently own two homes—one is my primary residence, and the other is a rental property.

Quote from @Adam York: Contact your insurance provider and let them know you intend to rent out the home.

There are a few programs that can do second position financing but typically underwritten based on your personal income.