If anyone has experience with taking over a mortgage, I’d appreciate your insight. 

In your experience, do you find that it's possible to cashflow or at least break even with these properties and today's prices/rates?

I'm wondering if anyone has had experience with a similar situation to mine and or has any advice.I'm looking to buy a triplex as well as a single family home that is on one parcel, so 4 total units.

Living with your tenants can be very challenging speaking from experience. 

I am assuming your a pretty dang good attorney, and with some experience under that belt given it's worth $500k+ to whoever, for you to do what you do.

Just by having those two traits they are in the top 25%, based on my experience. 

The experience/knowledge of being an agent will help you so much.  

By adopting the house-hacking method—living in one unit while renting out the others—we plan for the tenants to cover the mortgage and gain valuable property management experience.

Do people have experience doing so and have they been successful?

I've learned through my 4 years of experience within real estate that my strengths and best used in raising capital.