They seem to be procrastinators so my fear would be that they wouldn't do it at all.  

Devour any reading material you can access on RI and personal development, actively engage with members in the forums (and locally), and remember this (something I read), " ACTION CURES FEAR!"

It's to not have to worry about providing for my (future) family, and not live in an existential world of worry/fear of money like I did growing up.

This is one of my biggest fears and one of the reasons I've learned to not pay till the work is done.

I like the idea of owning a vacation rental, but feared that the management cost would be too much.

We are actively marketing in our target areas.)So, the last thing I will say is get educated and eliminate your fears.

You never had time to fear getting started.Bigger Pockets has various resources: ebooks, blogs, forums, podcasts, webinars, colleagues, keyword alerts, an awards system, a learn section, informative people in many fields of real estate, and more.If you have time consider spending 30 minutes for 30 consecutive days on Bigger Pockets.

I think the current owner is somewhat intimidated by the person renting and won't do anything to rock the boat in fear of losing her. 

Anything that I fear is teaching me courage to overcome. 

It allows the Wholesaler to advertise the property all day long, take out a billboard ad in front of the state real estate commission in Oho or any other state without fear of getting nailed!