if you were clearing 300 per month on your current property, and if a cashout refi puts that place into negative cf territory, your new income property investment must compensate for that loss. 

I could do that but I have very specific questions and I'm working abroad right now so I'm limited to online courses unfortunately (us territory of guam.)

These very quickly grow fast enough to put homeowners into negative equity territory, and as a general rule many homeowners often ignore their house payment problems for a long time before taking action.For the OP - there is no easy quick way to learn short sales.

I've run numbers on hundreds of rental properties at this point but this is entirely new territory to me so I'm not quite sure how to analyze the different options or where to even begin.For what it's worth, according to Rentometer, the median rent for a 3/2 SFR is $2100 and a 3/2 duplex would be around $1800.Zoning:X = Prohibited P = PermittedR/A = Permitted upon reviewed plans

(global implications are a bonus).For background wife and I recently had our first child, so this has become very top of mind and in terms of assets we are in the Qualified Client+ territory, mostly in public investments (index funds, equities, public REITs, bonds, cash) with a little in private (real estate, crypto).Appreciate any good recommendations.

I've never bought anything over 4 units so this is me wading into uncomfortable territory, but I do feel like with the right value adds over time this thing has the potential to be a great buy for me longterm.Thoughts?

I don't think there is any strategy out there that would eliminate the risk of a market dip as you described, so I just look at it as something that comes with the territory of short term real estate investing. 

4500 ft2 is McMansion territory size-wise, so is it a series of complicated shapes with a hump?

I guess it will come with the territory If I intend to scale.

No early repayment fee so we can pay it off in a few years if we want once more stock vests / reaches capital gains territory for selling.