Higher income due to newer properties and higher resale/refi due to the new build out 

For example, did he buy a business vehicle that he depreciates on his taxes over time?

If you're penciling it on, on your buy that's a bit optimistic and you'll have to likely understand your house value would then appreciate re-creating a re-finance loan with a new & higher tax basis and insurance which would likely not make it as affordable as you are penciling in.My best advice is to look to buy a value-add, something on the MLS for longer days or off-market.

Your operating expenses appear to exclude property management, which can be 8-10% of your rental income.4.

So I used the loss to offset other taxes, and repurchased the stocks to hold for when they rebound. 

I know that it is typically 20% gross income to have another company manage the property, but wanting to know the cost breakdown if I were to self manage.

We advise landlords to require two main criteria:1) Household income should be at least 40x the monthly rent.2) Applicants must have a credit score of 680 or higher.It's also important to review credit reports for red flags like rental collections or high credit card balances.

Could a long term lease could be written as a series of short term leases (less than 30 days), and thus qualify income from the rental as "Active" and thus allow the tax filer to file as a "real estate professional"?

How is the rental income.

Assuming you are not subject to penalties, do your analysis in after-tax dollars.