I recently closed my first conventionally funded investment property in Milwaukee, so currently I don’t have the funds to just run a conventional loan “house hack”.I have submitted pre approval requests to 4-5 VA loan-friendly lenders and each one is denied for the same reason as the last...

It's done by wholesalers all over the country by assigning the contract through whatever is the local convention for contract assignment.

Conventional And DSCR lenders will require a minimum of 15% down.

The good news is that you can still acquire this 4plex relatively cheaply with only 5% down using a conventional Fannie product.

Fannie Mae wouldn't purchase the loan if it didn't meet that requirement.As for a team in place, although that's good, you'll still need to show that you have actual experience managing real estate in some capacity.If you switch to a conventional loan, from VA, then you don't need to have management experience.

I don't believe DSCR would be the right way for you to go on this until you've exhausted all of your conventional options (and I'm a DSCR broker/lender).  

Hey Eli, Conventional mortgages (Fannie or Freddie) are not assumable. 

Usually after your first or second home under VA, you'll run out of entitlement and likely need to switch to conventional financing later on, unless you sell the previous homes that were originally acquired with VA financing. 

A few years back I bought a foreclosed property with the intent of using a conventional mortgage.

I think ADUs for househacks are the future for young professionals, and most of the conventional/govt lending guidelines were updated late last year to support this.