What I have found is that right around 2-4 properties, most people are tapped out on DTI and are unable to qualify using a conventional loan. 

What KEY things do I need to look for , that may disqualify these ( or any property for that matter ), for qualifying and going the VA Loan route ?

I highly recommend a well-qualified REALTOR who works with investors and knows how to help you best.7.

Seek advice from experienced investors and a qualified real estate agent for informed decisions.

I would like to know what all qualifies as completely clean here- Electrical wiring is normal and no unlicensed modifications - Structural inspection is also clean.Seller is ready to discount the price by ~20% from market plus the cost to repaint the whole house What are other questions to ask and things to consider in this scenario?

However, if it's your house, and it's in a good A/B area, and the rental comps have ceiling fans or other amenities that your house do not, your property might not attract the more qualified tenants. 

The lower the rate, the harder it is to qualify for these loans since they up the requirements. 

How many tenants would qualify for rentals if you couldn’t depend on them collecting minimum wage for their labor so they could pay rent?

It also might not qualify for some popular second home loan products.Lastly, it’s important to note that this COA is currently undergoing assessments for renovations, which may influence purchase prices.If you’d like a list of all the properties for sale here, please let me know!

The first of course being ability to repay (which borrower should qualify for in this instance since their payment is going down), but more importantly is the loan to value.