Best to start with your finances then target a location.  

This simple but powerful metric tells you how much vacancy your property can handle before it starts losing money.

Until this is addressed, hand wringing and clutching pearls while waiting for the Fed to lower rates is an exercise in futility.

Once you start profiting, understand how rental investment can wipe out your taxes.This post does not create a CPA-client relationship.

I would set the option term for 24-36 months from now as the time when he can exercise the option and adjust the price to account for expected appreciation with a discount applied for a $150/month of his rent prior to the transaction.  

It's not a bad way to start.

My two cents...slow down a bit and start building relationships rather than spending all of your time dreaming on zillow.

And what would you avoid if you were starting over today? 

Start using your own personal network to find motivated sellers. - Start posting on your favorite social media site what you are looking for – not once or twice, but CONSISTENTLY for 6 months!

I’m new to real estate investing and would like to start with Wholesaling with the aim of taking on fix and flip as well as short term rentals later.