This second property is in a MUCH improved neighborhood, which draws in a better class of tenant, it's professionally managed by a trusted company, and it's structurally sound with recent major improvements.WHAT'S NEXT??

Shortly after Roofstock acquired them I have seen improvements and haven't had issues with bank account connectivity.  

For an unrenovated 1+Den/1BA LTR in our section of Northeast though, $1,300-1,400/month is certainly in the ballpark of what I could comfortably get with some very minor improvements to the space between tenants.So all that being said, I think your target of $1,500-1,600/month for your 2BR units would be more than doable. 

I would make one distinction and that’s between an expense and a capital improvement. 

Here are the playersMe - OwnerOG Developer - Original Developer that improved property before I purchasedNew Developer - New Developer currently building a new subdivisionWater District - Own the vacant land that my sewer line runs acrossCity - Well, The cityTimeline:2007 - OG developer purchases large 1 acre lot with an existing house with the intent to subdivide and create a small PUD.2008 - Improvements are made (new street, sewerlines, storm, power, water) are brought into the subdivision. 

Improve the grade if water flows toward or pools near the house.

Would my previous industry experience (property management, acquisitions, asset management, Realtor) improve my chances of qualifying for a DSCR loan?

These loans allow buyers to purchase a property “AS IS, WHERE IS”.Renovation loans are available in 30, 20- and 15-year fixed rate terms and can be used to purchase owner occupied, second home and investment properties.By time the renovations are completed, the home needs to be in move-in, live-in condition and conceptually ready to be resold without repair issues.Other Important Items to Know about “Conventional” Renovation LoansMaximum – Minimum Purchase/Upgrade Amounts:Maximum: Limited to 75% of the “after improved” valueOccupancy: Primary, Second Homes, Investment PropertiesUnits: 1-4 unit propertiesRenovation Term:The renovation term for this program is a maximum of 180 days.The Borrower(s) is responsible for the work being completed within the escrow period.

@Jewell ArceneauxHow to drive ARV (my opinion)Improvements that drive the ARV the most: Roof, New Kitchen & Bathrooms, Flooring, PaintImprovements that DON’T drive the ARV as much: Windows, Landscaping, Driveway, Rough Plumbing & Electrical

And keep in mind that the rate on the 2nd lien will likely be 10-12% so depending on the cash flow it might not actually yield that much cash to you at closingMore importantly, it's just more debt so ultimately it sounds like you need an income-producing event to actually improve your situation and avoid some of the consequences that you mentioned