My question/concern is what I should do with my money now to prepare/enable me to purchase a second home in the future. 

Figure out what you want to do and then figure out whether a real estate license would help enable that.

If a sweeping bill doesn’t get traction in Congress, there is still a decent chance a narrower tax rate cut will get passed, according to lobbyists and Capitol Hill officials working on tax legislation.To finance such a rate cut, some in Congress have in their sights what’s known as the 1031 exchange provision, which enables sellers of real estate and other assets to defer capital-gains taxes by reinvesting the proceeds in “like-kind” properties.

This enables you to get into investing on the cheap and start learning.

Have it handicap-enabled and do a Senior Living (2nd floor may be unusable)7.

Here's the Homeaway statement re: the service fee:"We are announcing changes that enable us to provide the best experience and most value to travelers and vacation rental owners and managers.We are revising our traveler guarantees to provide even more coverage, reducing prices for owners and managers, and changing the way we monetize our business.Now, travelers who book or pay directly through HomeAway’s sites will have the full amount of their booking protected against things like misrepresented or double-booked properties.

The job would however enable you cash that you can leverage for the buy and hold deals.

Almost seems like you would be enabling the parent to live off the child instead of it being the other way around.

I have two rental property investments. 1 SFH in San Diego purchased in 2010 for 900k, currently valued at 1.4m, generating $5,500 in rent a month. 1 SFH (+ guest house) STR / Airbnb in Cabo Mexico purchased in 2016 f...

It enabled me to become self-employed over 4 years ago and I'm never looking back!