I came across a local developer who seemed to have a good reputation and a track record buying small to medium multi-families, doing some work refurbishing and repositioning the properties and flipping them in a couple of years.  

The good part is there is hardwood underneath.

I was either leaning towards a single family at first or multi-family

Have you considered multi-family instead?

In the long term, I would like to eventually transition into owning both SFRs as well as multi-family properties.  

I believe that you best bet would be to invest in multi-family.  

So I see the benefits for both parties so I think it can really work as long as one explains it clearly and honestly.

One idea is you can look into buying a multi unit and live in one unit, if that works for you. 

Real Estate is a agreement between two parties.

I want to learn more about flipping and buy and hold w/multi-family units.