Should I focus on teaching him the basics of personal finance, like saving and budgeting, or is there a way to introduce him to more advanced concepts like market analysis? 

Basically, you're gambling on the second appraisal and at most you will lose the $1000.  

That 2nd requirement is  what makes it close to basically impossible with a W2 job.

The rental had ratty furniture, a record player prominently featured in the marketing but it had no speakers, missing basics items in the kitchen, lots of drunks in the concrete hallways that reverberated right into the bedroom at 2am, a strong odor of urine outside, and more.We have super hosts in this forum that have hundreds of 5-star reviews and are masters of the craft, but I look at their rentals and see they don't have any artwork on the walls, decor is basic, they do nothing to make the guest feel welcome, etc. 

But, basically it's experience that wins the day.

You basically have no escape plan.

Finally the pro formas that they provide are absurdly basic and neglect at least 25% expenses, so are essentially useless. 

Quote from @Robert Gunn: I would also be very interested in hearing student or JV experiences with Pete and his program.I stumbled upon him by chance and for fun (I've been investing in land for years) signed up for his "free" course, which he promises after he pitches his $499/mo software system (which is basically an overpriced CRM) and then after the first "Level" in the course, you are directed to a pay page to access the rest of the "free" course.  

Educate the land owner on the potential profit run the numbers and go over the basic proxy and blue prints.Make sure you have a seasoned and qualified Builder/GC because they can be a deal killer with wasted time and inflated material and extended completion dates.

Basically, what I said was it would be good to get the best of both worlds.