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

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. 

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.

For example, if the listing is selling for 200% of the last purchase of two years ago with no improvements, etc.?

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

However, speaking from personal experience, if you are positive and work your *** off to improve your luck, you are going to be much luckier than those naysayers.So happy for you!

Additionally, considering the time value of money is crucial, as deferred gains and tax efficiencies may improve long-term returns despite upfront losses being largely on paper.

So much so that when we do come across that all-to-rare exception of a person who's grinding at improving there life, to elevate, it's notice, it's a shocker, and we go the extra mile to really help them if and where we can.