If they don't NEED the money for a down payment elsewhere, the income could certainly fund their payment at a new home, rental or retirement home. 

Risks: rates go down and you have to pay a prepay of 2 or 3 %; you have to sell and pay the prepay; rents decline & you can't make the payment like any other type of loan; cost upfront a little more than conventional; need to find experienced broker licensed in the state where subject property sits; servicers are bulldogs. 

Then if/when another good deal comes up, you can approach a lender and look at leveraging either of the properties in order to fund the down payment of the new property.

Treat this property as a business and factor in all the associated expenses, including mortgage payments (if you pull a loan), maintenance, and potential vacancy periods.To simplify management and make this less of a hands-on job, I’d strongly recommend working with a property management company.

., the appraisal for 5+ is at least $2k-$3k) and the financing structure by lenders because Fannie/Freddie don't generally buy loans for commercial properties.So, for you personally, the biggest driver for the type of your next property is probably going to be the amount of a down payment/equity you can put in the property.

The strategy I'm following for my first house hack is to acquire a multifamily property (duplex, triplex, quadplex) or SFH w/ an ADU (or potential for an ADU) as I am mainly looking to simultaneously acquire my first property and subsidize my mortgage payment.

.- There is no discount or created equity over and above the amount that is used as the down payment for the home.- The management company charges a management fee of 10% - 15% which can be a little higher than average property management companies, but that cost may be offset by higher quality of services.- The management company also charges for other services such as fee for coordinating maintenance and repairs, and turnover and releasing.

I have been digesting all things Real Estate so right now I am working to lower my DTI while saving at least 6-7% for the Owner Occupant down payment (to include closing cost, etc.).

Do you have a price range (or down payment target) and are you ok with some rehab or do you prefer turn key?

In a Subject To, it isn't the seller making the payments.