I would live in the house for at least 2 years (to avoid capital gains tax) before selling.

I don't want to go through this process only to be denied 30 days into an escrow period because the lender missed something.

Typically when you sell the title company requires forms to state if you are foreign or not, your ID, and they want to send 15% or 10% or (20% for long term) to the IRS at closing.

There is never any pressure to buy, and they offer a variety of consulting platforms to guide a potential owner through the process of purchasing passive real estate in Jacksonville, Florida.

Selling a house and agreed to terms with a buyer *pending inspection report*.

Make sure to think the entire process through as it may be more advantageous to to it prior to or after the purchase of the other property for your brother.

(Check out  this tool to automate above process: https://stateconcile.com/) 

- Buy something that you can add value to, refinance in a year or two (or when it makes sense), take the cash out and buy an investment property- Buy new construction, let the builders build the equity for you while you live there, sell in two years (or LTR - MTR typically isn't allowed in new construction neighborhoods)If you are thinking of self-managing, what about Winston Salem/Greensboro area?

Why would boomers have to sell?  

If you sell or leverage your 2 properties and use the $100k you have you to buy rentals you will not even come close to making as much in cashflow as you make with your current career.