Totally agree with you here (except one thing). The world in this game is binary in nature. If you don't do that, then this will go wrong. Things like that, that is not how I would see it working.

The one thing that I don't agree on is that

So, coming out a couple hundred dollars ahead, I could run this "poverty" scenario for 4 months and have enough to buy a refurbished MacBook Air and join the Apple Developer's Program, with which I could bootstrap an iOS App-writing business. Seems some others played, came out over $1000 ahead, and could jump in to app-writing in one month flat.

You are not coming out a couple hundred buck ahead. Tomorrow the landlord will require rent so minimum $800 in that, even if you are in a good job you have $200+$300, so you owe a little back rent of $300. But I doubt every single month will be so bad. I mean, my pet, friend and grandfather can die only once right?