@Kellen Bradford
I haven't done one yet myself but when I do, I'm definitely starting with one. From what I've read from other peoples' experiences, things come up out of nowhere. It would be devastating to overextend yourself and have the unexpected occur on FOUR projects, to the extent that you are unable to rent them and now you are stuck with four house payments, insurance, taxes, etc. and I assume you plan on having a primary residence, so five payments. Also, you probably would have financed a lot of the repairs, so you'll be paying project loans as well. $100k won't last long in this scenario.
Have you considered starting with a quad-plex, renting out three units and living in one? You would essentially be living for free since cash flow from the other three units should cover your payments. Then, when you are ready, move out (perhaps into another multifamily) and rent that last unit. If you are eager to get a bunch of rentals under your belt right away, this sounds to me like your best bet.
Whatever you do, keep us all posted. Good luck!