Ideally we would love to live in my childhood home.

I tell everyone this, New York is one of the hidden gems of investing if you know how to play the New York game.

You probably don't want to live next door to tenants; ideally, they would just think you're also renters. 

Ideally, this would be just one step in a larger plan to grow into multiple rental units over time.

@Lauren Ruppert Yes, an LLC can sell a property to your child’s LLC, ideally at fair market value (FMV) to avoid gift tax complications.

Something I would recommend from experience working with people is to figure out your ideal niche and stick to that, at least just starting out.

If there is no difference between Carrot and WordPress when it comes to SEO and ranking on GOOGLE then it might make sense to go with WordPress for a long-term play. 

Here is my Cliff Notes on this elaborate example:If you have unused losses from the past, they might significantly soften the tax blow from a profitable sale.I don't see how this is called "strategic play" or "premium lemonade."

Play the long game and hold onto that equity. 

You have to tell people if a toy is broken, missing pieces, or might explode when played with.