The cashflow and equity wouldn't just produce income; they'll produce wealth.As far as your lending questions go, find and talk to hard-money lenders in Fort Hood.

The issue we have run into is that our bank will not allow us to finance a new home until we prove our current property produces rent, and it has to be seen on our W2’s.

So, any other expenses aside, just one transaction could cover your expenses (depending on your price point)...Aside from costs, don't forget that brokerages tend to have the new agents "do stuff," e.g. sit the front desk, attend meetings, attend training, actually produce (since brokers make their money from producing agents)...Hope this helps. 

This scenario produces negative cash flow of around $100 per month out of my pocket.SCENARIO 2: 160 acres of grain producing farmland in Saskatchewan.

Luxury househacking a nicer place that happens to have an income-producing rental is still househacking.   

He has a bail of $25,000 but can get out at any time if he can produce $2,500. 

In this case it means going for lower risk investments that produce lower returns.

A DST is simply a separate legal entity created under the laws of Delaware to hold title to one or more income producing commercial properties.

I also have 32 single family rentals and an office building that produce 10-15k/month cash flow (before vacancy/repairs).

Or just rely on them to produce financials?