That's the best way to get into investing; holding the property you own and renting it when buying another.

Especially since you are looking at properties that are already high value.

Working with Property Managers – What should I look for in a good property manager to ensure smooth operations? 

We have properties out of state and use property managers.

I've used this strategy in a similiar situation wherein the repairs needed to the property were made part of the agreement and the tenant buyer took possession with repairs needed and fixed the property to livable condition.Also in the scenario I received $5.5K down payment on a 3 year term $1200 per month and P/I cost me $550 and I paid taxes and insurance. 

One of my clients recently asked about using the Short-Term Rental loophole for a property in a foreign country (Mexico).

My grandfather, along with his twin brother, were home builders who transitioned into building and managing a significant multi-family portfolio, which remains family managed to this day.With my personal family background, as an agent I have largely engaged in the multifamily space working with legacy owners in the sale of their properties - from 6 unit, single building properties to 19+ unit, multi-building properties.

You put QR code placards through your property for guests to see and browse.  

If you already have an experienced property management company to take care of the properties, then it wouldn't be that much of difference based on how they handle the properties.Typically you get more younger generations in the apartment buildings than any multi family homes.

To get to the next property, or any property.... you need cash.