If you can find opportunities like this to turn additional living space into a bedroom you can substantially increase your rent for the unit. feel free to reach out if you'd like; i'm an investor focused agent specializing in house hack opportunities.

Will be turning into a 4 bedroom home with complete main floor living.

Is it more profitable to turn a STR to a MTR for the winter months in a coastal town?

As long as they're paying and not damaging the property I would take that over having to turn the unit, handle a vacancy and then trying to find a better tenant in said C area.

Hey Account Closed - Check out your competition with furnished finder that is where a lot of Medium Turn rentals list their properties.I have a MTR in Chicago that has been decently successful...whatever I have found throughout my entire life and investing career is it is never one property/deal that is a grand slam...Rather, the grand slam is done by hitting many singles and using systems and processes to scale your operation; the combination of scaling and experience in a niche of real estate allows you to hit unlimited grand slams because, unlike baseball, real estate is NOT a zero-sum game.

And then you will purchase a new investment property and all of the gain is tax deferred indefinitely as @Jaron Walling said.The way to combine and get both advantages would be to move out and turn that property into an investment property for a year. 

I come from working with engineers, so I am used to it but I can absolutely see how others are turned off 100%. 

If it turns out the seller is a vet, you move up quickly.

There’s a learning curve in getting started but once you are in control of your own self once you turn 18 you will be free to buy a house hack and get started.

This months zip codes all produced an ROI of 7%!