If you continue to house hack, I see no reason why you should sell the property.If you did a 1031 exchange, are you able to cashflow greater and/or target a better an area with higher appreciation rates? 

If you plan on flipping or LTR, target those investors.

The target investment property looks like it will cash flow nicely! 

My name is Rachel - I currently live in the Washington, DC area but have ties to Spain and am making it a target to move there farther down the road. 

I've been searching on Zillow to see what's out there and in what condition—targeting Class B in a decent area with a focus on cash flow.

You seem to see more triple net on big national tenants, WalMart, Target, Chevron, or Burger King.

I've shifted my focus from weekend stays to targeting guests who need accommodations for 30+ days.

On the other hand, leverage could allow me to acquire multiple properties faster.Considering my circumstances (unknown target market, family support in Fort Wayne, long-term goals), what approach would you recommend?

I agree with @John Underwood on this @Diana Mulvihill.You should advertise them as hot tubs, but be clear on what you mean.

Go to Etsy and search for "rental property tracker," and you will find hundreds of nice spreadsheets to track 10-20 rentals, usually for under $10.Software has extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.