To be honest it cost a lot of extra money outside of the mortgage & bills plus a whole lot of will power to push through those years.

Short term rentals are a business - your own business - and it not only takes capital for that business to succeed, but willpower. 

It's a question of will-power not infrastructure.

If you have the willpower, to get up extra early everyday to market yourself, follow-up with clients, meet new prospects, and walk a client through initial application, to loan doc signing and funding, I highly recommend finding a side hobby to destress lol.You definitely need to prepare your mindset to think like an entrepreneur.

How much WILL power do you have?

A realtor that you are wanting needs to be new and fresh enough to the have energy and willpower to work their a#$ off, but also have some experience and education to bring to the party. 

Hey Guys/Gals,Looking for recommended reading specific to deploying self discipline and/or will power.

More energy than brains but that's OK cause will power can overcome inertia.2. 

The reason I think you are okay putting extra money in your Roth is because I'm a big proponent of hiding money from yourself; perhaps you can set up a savings account separate from your current one that you chose to have a direct deposit to from your current paychecks (only do this if you have the will power not to dip into it).

Will power?