Is your DSCR ratio greater than 1-meaning are you cash flowing (according to the lender's criteria of mortgage, property taxes and insurance (and HOA) if applicable).

How would that affect his tax situation if at all?

A lot of my investors are just buying A-class for the tax benefit and breaking even. 

@Zachary JensenIs it only depriciation or also insurance/re tax/mortgage costs?

Let's just imagine a scenario where you only have one property, and you don't use any PMSs or apps like Turno, for example.Cleaning and maintenance: 4 hours per weekRestocking supplies: 1 hour per weekResponding to inquiries and bookings: 2 hours per weekHandling guest concerns during stays: 1 hour per weekCreating and updating listings: 1 hour per weekManaging pricing: 1 hour per weekFinances and taxes: 2 hours per monthInspections and minor improvements: 4 hours per monthTotal estimated time per week: 12 hours, more or lessTotal estimated time per month: 26 hours, more or lessIf you do use pieces of software to automate your work, it can be even less.

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. 

He narrowly escaped the property tax sale on his primary home a few weeks ago.  

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.

Does that include taxes and insurance? 

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.