Honestly a “slow market” over the last 20 years has been 2 weeks to find a tenant.

., only have the last couple months' worth of data.

I did something similar just last year on a bigger scale and made sure I had 7 years for my balloon since I only put 16% down. 

Last year, the State Legislature amended the Property Condition Disclosure Act, removing the option to give a $500 credit to buyers and adding seven questions related to a home’s flood history and insurance requirements.Here is the link to the story. 

Then last option would be a "unsecured" personal loan where the bank offers up to $50K for example to pay off and consolidate debts.The 2nd and the personal loan will pay off debts and lower DTI and you might have enough left over for down payment or just use VA again.

I live outside of Madison and have been watching both markets for the last year or so. if you have any questions feel free to message me.

I've spent the last week or so trying to get the answer, but I can't get to the bottom of it. 

Are you suggesting that because their expenses exceed income they are OK with having a loss? 

It is landlord-friendly, and specific pockets have gone upwards of 2-4x in the last 5-10 years.

This extra layer of protection limits the possibility of litigation and losses due to damages.