After getting his license and expanding his rental porfolio he still finds it difficult to get financing strictly based on the deal.

@James Godbout are you able to live in the new purchase or strictly for an investment?

I have a strict AC out of window by October policy and I tell tenants to close storms if I pay heat. 

The reality though, is that it could have been run any way I wanted and the "conversion" is strictly for my exit as the end buyer will be an out of state multifamily investor.

Then invest in a property that is strictly a rental and cash flows.

I’m planning on renting ours out in the future as well and will have very strict criteria for my future tenant. 

If you are looking strictly for cash flow I would think that the midwest and south (specifically GA, MS, AL,TN) would be hard to beat.  

I would develop a strict investment criteria (house hack/duplex) and don't waiver. 

For our investment property I'm honestly considering setting some pretty strict criteria that will guarantee good cash flow and then just making offers on places that meet those criteria/ making low offers without seeing the properties.

Conventional loans routinely go down as far as 5% and sometimes 3% under certain first time buyer's programs.