It does actually work and you can pay down your cards pretty fast, once paid off cut up most of them and keep 1 or two for emergencies.In todays world you will probably always have a car payment and a mortgage, on the mortgage side you can make 1 extra payment per year and it will shave 5+ years off your mortgage.There is not quick way to get out of debt unless you hit the lottery, but if you focus on paying your debts down and start doing investments that don't take much money out of your pockets you will get out of it in no time.

If it's going to take a lottery win to be able to happen then a) how likely is that and b) are they going to want this house again or buy their new mansion?

I thought I had won the lottery until I found out that's about what the property is worth.

if a property can't cash flow and you are buying it on anticipation of increasing value, you might as well buy stocks or lottery tickets.

Lottery tickets...boom

Some neighborhoods, like ours, allow for a choice of two schools by right, and two more by lottery, for elementary. 

It is possible but to increase your odds considerably buy a lottery ticket as well.

Others suddenly think they won the lottery and take a hold position and see if anyone else will make them 6 figure offer (worth 30k).  

Lottery tickets

Yes, not everyone who buys a guitar thinks they can possibly be a rockstar, but nearly everyone who is trying to make it big, believes they can (kind of like the lottery), when in fact they can't due to how unlikely it is.