Is it a little more of a gamble?

We definitely sound very similar in our risk tolerance (and judging my your company name you may also have a background in "gambling"). 

So while it was a great call on your part, not many people out there want to gamble their money in anything.

Now, i dont gamble but this adwords thing turned into an obsession.

You might gain huge or you might lose your shirt but you are taking a gamble and not buying right when you purchase.

With a NPN, if occupied, you may not be able to gain entry, leaving x% to be a "true" gamble unless you can somehow speak with the occupant and gain entry.

You gambled, you lost.  

For me to even think about the second car I want a big discount on the gamble I will be able to clear title, repair the issues to make this a car I could maybe make a buck on.

If you just look at appreciation it's not any different from gambling.

Does your wife want you to play a game and gamble your money, or does she expect you to do your homework, learn the market, and invest in something that will bring maximum return with the smallest risk?