Keep in mind, when you go to get your the 2nd conventional owner occ loan, your "old" primary residence that you will turn into a rental the PITI mortage payment becomes a liability on your DTI calc and the rent payments from tenants becomes an asset.

We’ve saved up and were planning to pay down the loan and refinance it, likely into a primary residence conventional loan in December-January 2020 (6 months after VA loan refi) and then start renting it out in July 2021 when we move so that we could free up our VA loan benefit for a new primary residence at our new location.

Also, as mentioned above LLC’s are only eligible for commercial loans which are generally more expensive and worse terms than conforming conventional loans.Holding properties, when they are smaller single or multi family residential properties, is usually handled with insurance.

@Sammie Baker - if you're using conventional financing (FNMA/FHLMC) you are required to have a 6mo seasoning period between acquisition date (deed) and the new note date (closing). 

But you're paying 5% instead of 3.5% or so from a conventional lender.

I used a low money down conventional mortgage.

Live in it for a year, term and rate refi to a conventional loan then house hack va again.

Can my mom use money from a 1031 exchange and I use money from a conventional mortgage loan to buy a house together?

@Suzanne Reilley and @Mitch Foster for self employed borrowers, if you're interested in a non conventional income analysis there are several options.

My experience is once my DTI ratio got too high I had to go the hard money route because I wouldn’t qualify for conventional financing, so I opened up a LLC to get financing through a Hard money Lender.