Without going into too much detail, my current job has put me in a somewhat unique situation of having a enough capital to begin investing with from a signing bonus, but not having a stable or high enough income with which I think I could qualify for conventional loans.

I do believe there could be some unique opportunities in the next 2-4 months. 

I'm frankly surprised that your attorney suggested combining them.

If you put together good systems you can avoid that somewhat, but I can say that I deal with more problems on my one property in a C class neighborhood than I do on all of my other properties (which are in B class areas) combined. 

I have an investment now where my net cash flow is more than my Mortgage (PITI), water, and utilities combined.

My first and HELOC combined are $510000 and I wanted to pull out $100K to invest in another investment property. 

Sell it now, net gain about $40-$60K after taxes, commissions, listing price, etcTo properly and adequately answer this question, one would need to know your strategy and goals.Strategy A is based on cash flow to support living expenses.Strategy B is long term wealth building - appreciation (market and forced) combined with principle pay down, depreciation, etc.If you strategy is A, then you should sell as this will not turn out positive for several years down the road (unless you utilize some sort of house hack play, vacation rental to increase income, or any combo of increasing income and reducing operating expenses - which by the way you skipped a lot of those in your analysis so your negative monthly cash flow is actually greater than you explained.)If your strategy is B, then by all means keep it and enjoy the likely future appreciation, amortization and depreciation deductions to offset your actual loss each month until the unit goes cash flow positive.

This type deal is not uncommon in Memphis, and out of state investors get burned when they focus on the paper returns and don't realize the unique challenges presented by the tenant class.

Combine that with losing the value of compounding, usually makes 401k/IRA loans a losing proposition.

My wife and I drive a combined 10k miles a year, are those of you driving 15k miles each per year willing to pay triple me?