I currently work as an independent contractor, and write off just about everything as business expenses, which leaves my adjusted gross income at next to nothing, making it hard to qualify for traditional financing.

Great job, though did you gross $247,000, with last one profiting you $140,000?

Gross expenses $24k.  

The last few years I've been pulling in over 20k gross rent.

Within the next year I expect he'll own 7-8 houses in cash, each worth around or a little over 100k, and each earning about $1000-1300/mo gross rent.

Assuming all 2 bedroom units, and assuming getting $700/month for them (leaving $163 for utilities) gross monthly rent would be ~$11,200Using pretty standard expenses, and a USDA loan, my numbers show this losing almost $10,000 a year.If I do some eraser math and make construction costs all-in at $75 per square foot, it winds up making around $12,000 year (with a CoC of around 10% using USDA money.)

Never use GROSS return for Cash-on-Cash calculation!

The net sale amount is computed by taking your gross sale price of $215,000 and then subtracting your routine and permissible selling expenses, which generally include your broker's commission, owner's title insurance premium, escrow/closing attorney fees, recording fees, exchange fees, etc.  

I gross around 65k a yearI have a house I bought at 22 years old for 204,900 with 0 down through a VA loan.  

Here are the numbers that I'm using:After Repair Value = $150,000Desired Wholesale Profit = $5,000Cash Buyer's Desired Cash on Cash Return = 12%Loan Amount = $100,000Loan Interest Rate = 5%Amortized = 30 yearsPurchase Closing Cost = $3,500Total Gross Monthly Rent = $1,800Other Monthly Income = $50Property Taxes =  $1,350Monthly Insurance = $45Vacancy Rate = 8%Repairs = 8%Cap Ex = 5%Property Mgmt = 10%So based on these numbers I'm calculating $150,000 - $18,000 (12% COC) - $25,000 - (not sure what's considered fixed cost) - $5,000 = $102,000 but the calculators states that my MAO is $124,767.84.