Challenges could include:Having the population to make it a sustainable day-to-day venture.Finding quality staff is tough these days, don't care what you pay them.Breakdowns/serviceInclement weatherPennies on the dollar at exit If the truck does say, 1000 bucks and after labor/cost of goods the operator's left with 500 - 600, then has commissary expenses and a possible split with a partner(s)Ehhhhh...burnout.There were dozens of trucks here 5 years ago and only a handful have really survived the grind. 

First option leaves me with a paid off home and a slow start on acquiring properties. 

The downside is it takes time and a lot of money for it to produce results.

It's basically part 2 to that book and a must read.

Thinking out of the box, having a motivating "why" and a few tools in your arsenal you can definitely do it.

So my understanding of the lease then is that I can only charge a termination fee of a month and a half's rent.

USA Today , New York Times, local newspaper, local real estate agent, local business magazines and a few national real estate websites

Prosper has found over time that very few investors are using the secondary market and, as such, has made the decision to no longer offer this service.

I told him I will pay to move and a storage unit for any items he wants to keep from the vacant two year house and pay all fees he has. how do I pull him on the boat?

Great way to get equity in a deal with no money, just sweat and a loan.BTW, unless it is another family member, no one is going to lend you money on that deal.