New Home: I would need to dump some of my brokerage accounts for the downpayment(so some capital gains taxes would need to be paid to finance the downpayment on the new house) or if I sold our "current residence(2nd home)" I wouldn't need to.I understand the tax incentive of selling within 5 years of living there for 2 years, however, the cash flow seems larger then what I would get taking the money and investing in new RE in the future. 

Otherwise you will have to pay higher rental mortgage rate.4) If all goes well, you buy your new home to live in with FHA 3% down or FNMA 5%+ down and rent out unit you were living in. 5) Yes, you may have negative cashflow on the rental for the next 1-3 years, until rents increase, but this is part of investing.Be sure to calculate any changes in the rental property taxes and home insurance resulting from you moving out.

I'm going to have to crunch a lot of numbers for the loan, property tax, maintenance (which should hopefully be low on new builds), and I have to figure out how to obtain an insurance policy for the units. 

DSCR loans deal with the amount of rents the property will throw off minus insurance and tax liability. 

The taxes on this property according to the listing is $15,000.

Does that include taxes and insurance? 

I work with a handful of investor friendly lenders that don't require W2s or tax returns (lending is based on the property not the borrower) but am always exploring new avenues.

I have a fund seeking to make section 8 investments on 4 or fewer unit properties in landlord and tax friendly states such as Nevada, Florida, South Dakota, Utah, and Tennessee. 

Did your tax pro suggest this?  

I'm curious on how best to structure this approach: Who owns what, who gets what, rental income & depreciation (all tax treatment).