Remember, every dollar not going into a tax deferred vehicle is reduced by the relative tax rate by the time it gets to your pocket.    

Within the next 5 years he needs to be transferring all investments to a secure guaranteed investment vehicle.

Being remote as a newbie without scale you give up way too much control ... control and leverage are what makes RE such a great investment class in the first place, and leverage without control is very dangerous, so if you are going to give up control (whether you admit it or not) then you are best served by looking at other investment vehicles.

I considered buying it to do what my original goal was, which is a place to live personally with enough space to put a house for my mother in law and some garages/carports to house my vehicles ( I am in the ground transportation business).

It's a small lot (a little less than a half acre) and my idea was to just put up a steel building/garage and use to store classic and/or restored vehicles in.  

Pulling a LOC on your vehicle/tractor?

I want to use whole sailing as a vehicle to pay down my debts and and eventually buy and hold properties for passive income.I was introduce to the concept of wholesaling real estate e few years ago by one of my college teammates.

How do you think self driving / autonomous vehicles will impact the value of real estate? 

You can put a hitch on just about any vehicle so I'd start with that.

A little history, I defaulted on 2 vehicles  settled a LOC and credit 4 and 3 years ago respectively.