Getting First Property From Your Current Landlord?

[Austin Dadisman]

Hi BP! Trying to get my first interaction here :)

So I've finally finished one of Brandon Turner's books on "Rental Property Investing" and I've now started "Investing in Real Estate with No (or Low) Money Down". While reading I had a thought - I know that my current landlord is an older man with many properties using a property management company by talking to my neighbors. The house I live in is great, but not necessarily updated, and the area is booming thanks to large local areas to work. The neighborhood is very safe and near good school districts and a growing economy (restaurants, leisure activities, near the interstate but not BY the interstate). I'm on the east coast in SC, in the upstate area, so the job market is a lot of blue collar manufacturing and very steady/secure.

My goal is to build a portfolio of SFH rental properties here, as that's what my area affords me. Multi-family properties are few and far between, and based on the numbers aren't worth the hassle.

Here's my question - Has anyone had success or know of strategies of talking to your current landlord hidden behind the PM screen? I'd like to see if he'd possibly do seller financing, a lease option, or some other creative finance strategy to allow me to make the home mine to rent out myself, while still being a win for him and his cashflow. If not, I'd like to see if he has any other property he'd be open to doing the same with, or at the bare minimum talk to me about real estate and possibly get me that jump start/boost I'm seeking. Have any of y'all done this before or have any helpful advice as to where to start? I don't want to approach him out of the blue and hammer him with questions. How would y'all start a relationship without being desperate?