If you're under the assumption that rates will be higher next year, then maybe you start to ramp things up this year...and if the right place comes along, you don't wait on it....vs waiting until you have 20% down, which is not necessary. 

I would ask a CPA, which I am not.My assumption is you would treat 1/2 the duplex as a rental and depreciate it as such and treat the other half as a personal residence, taking a mortgage deduction but not depreciation.

. ($550k * 94% = $517k) (Original loan balance of $353k) ($517k - 353k = $164k) ($164k - $127k = $37k) (Don't know how much principal you've paid down since buying, hence the assumption of about $40k). 

Assumptions are as follows: $75k purchase (no discount), $1350 rental income, $15k rehab budget, 30 year mortgage at interest rate of 6.0%.

Alternatively, you can postpone filing your return until Congress definitively approves or denies the deduction for 2018.However, once your adjusted gross income (AGI) exceeds $100,000 ($50,000 for married filing separately) the deduction is reduced.The above tax assumptions are provided for reference only.

Any ways I can improve my analysis process/assumptions? 

You seem to be operating under either of two erroneous assumptions: 1. the licensure board has authority to regulate all real estate transactions in the Commonwealth--they do not, they regulate any person acting as an agent that participates in them for a fee; and 2. that assigning a contract or making a profit on selling property creates an agency or a fiduciary relationship--it could, but not when done properly.

@Kyle Mitchell this is not common, you want to get them and verify your assumptions before buying the deal.

Assumptions here are that you have paid off the real estate involved, your net operating income (rent-expenses except for mortgage-NOI) is at 50% of rent and rent will keep roughly in line with inflation.

Plus the acquisition cost per unit is usually lower, the more units you buy at once.It's tough to talk in generalities though because I find prices in student areas are often inflated on the assumption that the landlord will definitely be renting to students by the room.