I currently have 3 WeMo on/off light switches and a couple of plug in light switches.
I am planning to get some Z-wave light switches for my 3-ways (Zooz seems to make the switches that work the way I want).
1) Can you clarify this question - I'm not sure I understand what you're talking about. By outlet are you referring to a junction box or an electrical outlet (plug)?
2) Wemos require hot, neutral and ground. AFAIK, most smart switches at the very least want a neutral wire.
3) Wemos don't need a gateway (wifi), but they know their status.
If I could do it all over again, I probably would have skipped Wemo and went with Zwave instead.