I don't want to resort to my family, and instead show them that i can become wealthy without their money.

But if I bought and held properties, isn’t that a path to wealth?  (I

I also wish I would have had a better understanding that the first property, while not making me wealthy, would provide me with a ton of information and ways to learn about the best ways to move forward.

True wealth is obtained from the appreciation and many tax benefits from residential RE investing.

BUT the way they did it was bought the properties outright (very wealthy family) and just live off the rents.

Tom, I used to work in insurance, and I had a (wealthy) customer who bought a Ferrari, but who was afraid to drive it much because the resale value drops significantly with every passing mile.

Though there is absolutely nothing wrong with building personal wealth, I think, as you've come to see, that financial goals alone, are ever moving and never ending.  

If you are talking to wealthy people re: Private Lending, the best book I know is "Values Based Selling" by Bill Bacharach.

However, most of the time these homeowners who have multiple properties are sharp, wealthy individuals who have retained councel and advise from their CPA's and they understand that they will probably have to pay some sort of difficency judgement and will be issued a promissary note.

I need a vehicle that can drive long distances at the drop of a hat without having to worry about 30 minute stops every 200-300 miles to recharge.Would I consider a Tesla if I was as wealthy as some of the big boys on this thread and could afford multiple vehicles?